US8841265B2 - Composition comprising triterpene saponins and compounds with angeloyl functional group, methods for preparing same and uses thereof - Google Patents
Composition comprising triterpene saponins and compounds with angeloyl functional group, methods for preparing same and uses thereof Download PDFInfo
- Publication number
- US8841265B2 US8841265B2 US12/344,682 US34468208A US8841265B2 US 8841265 B2 US8841265 B2 US 8841265B2 US 34468208 A US34468208 A US 34468208A US 8841265 B2 US8841265 B2 US 8841265B2
- Authority
- US
- United States
- Prior art keywords
- group
- angeloyl
- acetyl
- compound
- sugar moiety
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related, expires
Links
- 125000005601 angeloyl group Chemical group 0.000 title claims description 292
- 150000001875 compounds Chemical class 0.000 title claims description 280
- 238000000034 method Methods 0.000 title claims description 50
- 239000000203 mixture Substances 0.000 title abstract description 34
- 125000000524 functional group Chemical group 0.000 title description 7
- 229930182493 triterpene saponin Natural products 0.000 title description 2
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 50
- 206010061535 Ovarian neoplasm Diseases 0.000 claims abstract description 26
- 208000000453 Skin Neoplasms Diseases 0.000 claims abstract description 13
- 235000000346 sugar Nutrition 0.000 claims description 240
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 188
- 125000002252 acyl group Chemical group 0.000 claims description 173
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims description 112
- WQZGKKKJIJFFOK-SVZMEOIVSA-N (+)-Galactose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-SVZMEOIVSA-N 0.000 claims description 100
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 claims description 92
- -1 alkenoyl Chemical group 0.000 claims description 74
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 claims description 69
- 239000002253 acid Substances 0.000 claims description 69
- 125000000217 alkyl group Chemical group 0.000 claims description 67
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 66
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 65
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 64
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 62
- PNNNRSAQSRJVSB-UHFFFAOYSA-N L-rhamnose Natural products CC(O)C(O)C(O)C(O)C=O PNNNRSAQSRJVSB-UHFFFAOYSA-N 0.000 claims description 58
- IAJILQKETJEXLJ-RSJOWCBRSA-N aldehydo-D-galacturonic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-RSJOWCBRSA-N 0.000 claims description 46
- AEMOLEFTQBMNLQ-DTEWXJGMSA-N D-Galacturonic acid Natural products O[C@@H]1O[C@H](C(O)=O)[C@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-DTEWXJGMSA-N 0.000 claims description 37
- AEMOLEFTQBMNLQ-WAXACMCWSA-N alpha-D-glucuronic acid Chemical compound O[C@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-WAXACMCWSA-N 0.000 claims description 37
- AEMOLEFTQBMNLQ-UHFFFAOYSA-N beta-D-galactopyranuronic acid Natural products OC1OC(C(O)=O)C(O)C(O)C1O AEMOLEFTQBMNLQ-UHFFFAOYSA-N 0.000 claims description 37
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 claims description 27
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- 125000001488 beta-D-galactosyl group Chemical group C1([C@H](O)[C@@H](O)[C@@H](O)[C@H](O1)CO)* 0.000 claims description 25
- SHZGCJCMOBCMKK-JFNONXLTSA-N L-rhamnopyranose Chemical group C[C@@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O SHZGCJCMOBCMKK-JFNONXLTSA-N 0.000 claims description 18
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 claims description 16
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- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
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- 125000000328 arabinofuranosyl group Chemical group C1([C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims 3
- SRBFZHDQGSBBOR-HWQSCIPKSA-N L-arabinopyranose Chemical compound O[C@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-HWQSCIPKSA-N 0.000 claims 1
- 125000005640 glucopyranosyl group Chemical group 0.000 claims 1
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- 150000008130 triterpenoid saponins Chemical class 0.000 abstract description 25
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- 125000005607 tigloyl group Chemical group 0.000 description 165
- 229930182490 saponin Natural products 0.000 description 79
- 235000017709 saponins Nutrition 0.000 description 79
- 150000007949 saponins Chemical class 0.000 description 75
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 65
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 62
- 125000003118 aryl group Chemical group 0.000 description 55
- SRBFZHDQGSBBOR-SOOFDHNKSA-N D-ribopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@@H]1O SRBFZHDQGSBBOR-SOOFDHNKSA-N 0.000 description 54
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 53
- PNNNRSAQSRJVSB-BXKVDMCESA-N aldehydo-L-rhamnose Chemical compound C[C@H](O)[C@H](O)[C@@H](O)[C@@H](O)C=O PNNNRSAQSRJVSB-BXKVDMCESA-N 0.000 description 40
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
- 201000003176 Severe Acute Respiratory Syndrome Diseases 0.000 description 34
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- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical group C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 30
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 30
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 25
- 229910052799 carbon Inorganic materials 0.000 description 25
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- 229940079593 drug Drugs 0.000 description 22
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- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 21
- 0 *[C@H]1CC[C@@]2(C)C(CC[C@]3(C)C2CC=C2C4CC(C)(C)[C@@H](C)[C@H](C)[C@]4([4*])[C@H](O)[C@H]([3*])[C@]23C)C1(C)C Chemical compound *[C@H]1CC[C@@]2(C)C(CC[C@]3(C)C2CC=C2C4CC(C)(C)[C@@H](C)[C@H](C)[C@]4([4*])[C@H](O)[C@H]([3*])[C@]23C)C1(C)C 0.000 description 20
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- XBZYWSMVVKYHQN-MYPRUECHSA-N (4as,6as,6br,8ar,9r,10s,12ar,12br,14bs)-10-hydroxy-2,2,6a,6b,9,12a-hexamethyl-9-[(sulfooxy)methyl]-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid Chemical compound C1C[C@H](O)[C@@](C)(COS(O)(=O)=O)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CCC(C)(C)C[C@H]5C4=CC[C@@H]3[C@]21C XBZYWSMVVKYHQN-MYPRUECHSA-N 0.000 description 16
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- SHZGCJCMOBCMKK-DHVFOXMCSA-N L-fucopyranose Chemical compound C[C@@H]1OC(O)[C@@H](O)[C@H](O)[C@@H]1O SHZGCJCMOBCMKK-DHVFOXMCSA-N 0.000 description 11
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- AFVLVVWMAFSXCK-UHFFFAOYSA-N α-cyano-4-hydroxycinnamic acid Chemical compound OC(=O)C(C#N)=CC1=CC=C(O)C=C1 AFVLVVWMAFSXCK-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7012—Compounds having a free or esterified carboxyl group attached, directly or through a carbon chain, to a carbon atom of the saccharide radical, e.g. glucuronic acid, neuraminic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/575—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of three or more carbon atoms, e.g. cholane, cholestane, ergosterol, sitosterol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
- A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
- A61K31/704—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/77—Sapindaceae (Soapberry family), e.g. lychee or soapberry
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/24—Condensed ring systems having three or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/24—Condensed ring systems having three or more rings
- C07H15/256—Polyterpene radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
-
- C07C2103/52—
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/52—Ortho- or ortho- and peri-condensed systems containing five condensed rings
Definitions
- This invention relates to saponins, and compounds with angeloyl groups isolated from plants, their uses and functions, and methods of their preparations.
- This invention provides a compound comprising a triterpenoidal saponin, triterpenoid, triterpenoidal compound or sapongenin, comprising two angeloyl groups, or at least two side groups selected from the group consisting of: angeloyl groups, tigloyl groups and senecioyl groups, wherein the side groups are attached to carbon 21, 22 or/and 28 of triterpenoidal saponin, triterpenoid, triterpenoidal compound or sapongenin backbone.
- This invention provides a composition for inhibiting tumor cell growth, comprising an appropriate amount of a triterpenoidal saponin, triterpenoid, triterpenoidal compound or sapongenin, wherein the triterpenoidal saponin, triterpenoid, triterpenoidal compound or sapongenin comprises two angeloyl groups or any two side groups selected from the group consisting of: angeloyl groups, tigloyl groups and senecioyl groups, wherein the side groups are attached to carbon 21 and 22 of triterpenoidal saponin, triterpenoid, triterpenoidal compound or sapongenin backbone. In an embodiment, the side groups are attached to carbon 21, 22 or/and 28 of triterpenoidal saponin, triterpenoid, triterpenoidal compound or sapongenin backbone.
- This invention provides a composition for inhibiting tumor cell growth, comprising an appropriate amount of a triterpenoidal saponin, triterpenoid, triterpenoidal compound or sapongenin, wherein the triterpenoidal saponin, triterpenoid, triterpenoidal compound or sapongenin comprises two angeloyl groups or any two side groups selected from the group consisting of: angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, dibenzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl, wherein the side groups are attached to carbon 21 and 22 of triterpenoidal saponin, triterpenoid, triterpenoidal compound or sapongenin backbone.
- the side groups are attached to carbon 21, 22 or/and 28 of triterpenoidal saponin, triterpenoid, triter
- the invention provides the methods and uses of triterpenoidal saponins purified and isolated from plants.
- compositions comprising the triterpenoidal saponins or their derivatives for inhibition of tumor growth.
- the compounds comprise angeloyl group(s) or tigloyl group(s) or senecioyl group(s) or combinations thereof which are attached to carbon 21, 22 or/and 28 of their sapongenines.
- the compounds may comprise any two angeloyl groups or tigeloyl groups or senecioyl groups or combinations thereof attached to a sugar moiety which bonds to carbon 21 or 22 of their sapongenines.
- the side groups are attached to carbon 21, 22 or/and 28 of triterpenoidal saponin, triterpenoid, triterpenoidal compound or sapongenin backbone.
- compositions comprising the triterpenoidal saponins or their derivatives for inhibition of tumor growth.
- the compounds comprise angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, dibenzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl or combinations thereof which are attached to carbon 21, 22 or/and 28 of their sapongenines.
- the compounds may comprise any two angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, dibenzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl or combinations thereof attached to a sugar moiety which bonds to carbon 21 or 22 of their sapongenines.
- the side groups are attached to carbon 21, 22 or/and 28 of triterpenoidal saponin, triterpenoid, triterpenoidal compound or sapongenin backbone.
- the saponin comprises a sugar moiety, wherein the sugar moiety comprises at least one sugar, or D-glucose, or D-galactose, or L-rhamnose, or L-arabinose, or D-xylose, or alduronic acid, or D-glucuronic acid or D-galacturonic acid, or their derivative thereof, or the combination thereof.
- FIG. 1 shows structure of saponins.
- FIG. 2 shows structure of saponins.
- FIG. 3 shows structure of saponins
- Positions 23-27, 29-30 are attached with CH3 or CH2OH or COOH or acetyl group
- FIG. 4 shows structure of saponins
- FIG. 5 shows a structure of saponins
- positions 23-27, 29-30 are attached with CH3 or CH2OH or COOH or acetyl group
- FIG. 6 shows a structure of saponins
- positions 23-27, 28-30 are attached with CH3 or CH2OH or COOH or acetyl group
- FIG. 7 A shows a structure of saponins
- FIG. 7 B, C, D shows a structure of saponins
- Position 23-27 and 28-30 are attached with CH3 or CH2OH or COOH or CHO
- FIG. 8 shows a structure of saponins:
- FIG. 9 A shows a structure of saponins:
- FIG. 9 B shows a structure of saponins:
- FIG. 10 shows a structure of saponins:
- FIG. 11 A shows a structure of saponins:
- FIG. 11 B shows a structure of saponins:
- FIG. 12 A shows a structure of saponins:
- FIG. 12 B shows a structure of saponins:
- FIG. 13 shows a structure of saponins:
- FIG. 14 shows a structure of saponins:
- FIG. 15 shows a structure of saponins
- FIG. 16 A, 16 B shows a structure of saponins
- FIG. 17 shows a structure of saponins
- FIG. 18 shows a structure of saponins
- FIG. 19 shows a structure of saponins
- FIG. 20 shows a structure of saponins
- FIG. 21 shows a structure of saponins
- Position 23-27, 29, 30 are attached a CH3 or CH2OH or COOH or acetyl group
- Positions 28 CH3 or CH2OH or COOH or acetyl group or angeloyl or tigloyl or senecioly or sugar chains
- FIG. 22 shows a structure of saponins
- S1 sucgar moiety one or more sugar, D-glucose, D-galactose, L-rhamnose, L-arabinose, D-xylose, alduronic acid, D-glucuronic acid, D-galacturonic acid or/and their derivatives.
- Positions 23-27, 29, 30 are attached a CH3 or CH2OH or COOH or acetyl group.
- Position 28 CH3 or CH2OH or COOH or acetyl group or angeloyl or tigloyl or senecioly or sugar chains
- FIG. 23 shows a structure of saponins
- Positions 23-27, 29, 30 are attached a CH3 or CH2OH or COOH or acetyl group
- Position 28 CH3 or CH2OH or COOH or acetyl group or angeloyl or tigloyl or senecioly or sugar chains
- FIG. 24 shows a structure of saponins
- Positions 23-27, 29, 30 are attached a CH3 or CH2OH or COOH or acetyl group
- Position 28 CH3 or CH2OH or COOH or acetyl group or angeloyl or tigloyl or senecioly or sugar chains or sugar chain with angeloyl group
- FIG. 25 shows a structure of saponins
- Positions 23-27, 29, 30 are attached a CH3 or CH2OH or COOH
- Position 28 CH3 or CH2OH or COOH or acetyl group or angeloyl or tigloyl or senecioly or sugar chains or sugar chain with angeloyl group.
- FIG. 26 shows a structure of compounds with angeloyl groups
- FIG. 27 shows a structure of saponins
- FIGS. 28 A and B shows the comparison of potency of Compound Y (saponin with 2 angeloyl groups) and compound X (saponin with 1 angeloyl) in ovarian cancer cells.
- the IC50 for Compound Y in ovary cells is about 1.5 ug/ml while the IC50 for compound X is 30 ug/ml.
- FIG. 28 C shows the inhibition of the purified Compound Y on the growth of skin cancer cell.
- the IC50 is 0.23 ug/ml.
- FIG. 29 shows the inhibition of the purified Compound Y1 and Compound Y2 on the growth of ovarian cancer cells.
- FIG. 30 shows the anticancer activity of Y, Y8, Y9 and Y10 on ovarian cancer cells as determined by MTT assay.
- FIG. 31 shows a compound of the invention without angeloyl groups.
- (B) shows a compound of the invention without sugar moiety.
- FIG. 32 shows a comparison of MTT and Haemolytic activities of saponin compound and Compound Ys of the invention.
- (A) and (B) shows hemolytic activities.
- (C) and (D) show MTT activities.
- FIG. 33 shows the saponin compounds Y, X ACH—Y, AKOH—Y of the invention. These compounds are purified and their structures were verified by NMR and MS. These compounds are then used for cell growth inhibition studies (MTT).
- Removal of sugars from Y (ACH—Y) but retaining the diangeloyl group retains 40% of activity (IC50 9.5 ug/ml).
- AKOH—Y removal of both angeloyl groups from C21 and C22 of Y completely abolishes its activity (no activity even at 120 ug/ml).
- Results indicate that diangeloyl groups in compound Ys are important for anti-tumor activity.
- This invention describes the results of a program of screening the bioactive compounds from natural plants. Most of the plants are in Sapindaceae family, which has 1400-2000 species with 140-150 genera.
- the program of screening for bioactive compounds is based on our purification methods and biological assays including the MTT assay.
- the invention provides methods and uses of saponins including triterpenoidal saponins purified or isolated from plants in the following genus:
- Saponins including triterpenoidal saponins may also be purified or isolated from the following species of plants:
- Acer campestre L. Acer chienii Hu et Cheng, Acer chingii Hu, Acer davidii Franch, Acer laxiflorum Pax, Acer mandshuricum Maxim., Acer mono Maxim., Acer orientale L., Acer palmatum Thunb., Acer sinense Pax, Acer wilsonii Redhd., Acer yui Fang, Aesculus arguta, Aesculus assamica Griff., Aesculus californica (Spach) Nutt., Aesculus chinensis Bunge, Aesculus chinensis var.
- Harpullia alata F. Mueller Harpullia arborea (Blanco) Rdlk., Harpullia austro - calcdonica Baillon, Harpullia camptoneura Radlk., Harpullia cauliflora K. Schum. & Lauterb., Harpullia crustacea Radlk., Harpullia cupanoides Roxb., Harpullia frutescens F. M. Bailey, Harpullia giganteacapsula M. Vente, Harpullia hillii F.
- This invention provides a compound comprising the structures recited in FIGS. 1 to 27 .
- This invention provides a compound comprising a triterpenoidal saponin, triterpenoid, triterpenoidal compound or sapongenin, comprising two angeloyl group or at least two side groups selected from the group consisting of: angeloyl groups, tigloyl groups and senecioyl groups, wherein the side groups are attached to carbon 21 and 22 of triterpenoidal saponin, triterpenoid, triterpenoidal compound or sapongenin backbone.
- the saponin comprising a sugar moiety
- the sugar moiety comprises at least one sugar, or D-glucose, or D-galactose, or L-rhamnose, or L-arabinose, or D-xylose, or alduronic acid, or D-glucuronic acid or D-galacturonic acid, or their derivative thereof, or the combination, thereof.
- a sugar moiety is a segment of molecule comprising one or more sugar group.
- compositions comprising the structures recited in FIGS. 1 to 27 , or a compound comprising a triterpenoidal saponin, triterpenoid, triterpenoidal compound or sapongenin, comprising at least two side groups selected from the group consisting of: angeloyl groups, tigloyl groups and senecioyl groups, wherein the side groups are attached to carbon 21, 22 or 28 of triterpenoidal saponin, triterpenoid, triterpenoidal compound or sapongenin backbone.
- compositions are obtainable from the above-identified plants.
- composition comprising the structures recited in FIGS. 1 to 27 , or a compound comprising two angeloyl groups or at least two side groups selected from the group consisting of: angeloyl groups, tigloyl groups and senecioyl groups,
- This invention provides uses of the saponins isolated from the roots, kernel, leave, bark, stem, husk, seed, seed shell or fruit of the above plants, and methods of their preparations.
- This invention provides a method of preparing the saponins, comprising the steps of:
- HTB-9 (bladder), HeLa-S3 (cervix), DU145 (prostate), H460 (lung), MCF-7 (breast), K562 (leukocytes), HCT116 (colon), HepG2 (liver), U2OS (bone), T98G (brain), SK-MEL-5 (Skin) and OVCAR-3 (ovary).
- Cells were grown in culture medium (HeLa-S3, DU145, MCF-7, Hep-G2 and T98G in MEN (Earle's salts); HTB-9, H460, K562, OVCAR-3 in RPMI-1640; HCT-116, U2OS in McCoy-5A) supplemented with 10% fetal calf serum, glutamine and antibiotics in a 5% CO 2 humidified incubator at 37° C.
- culture medium HeLa-S3, DU145, MCF-7, Hep-G2 and T98G in MEN (Earle's salts); HTB-9, H460, K562, OVCAR-3 in RPMI-1640; HCT-116, U2OS in McCoy-5A
- MTT Assay The procedure for MTT assay followed the method described in (Carmichael et al., 1987) with modifications.
- Cells were seeded into a 96-wells plate at concentrations of 10,000/well (HTB-9, HeLa, H460, HCT116, T98G, OVCAR-3), 15,000/well (DU145, MCF-7, HepG2, U2OS), or 40,000/well (K562), for 24 hours before drug-treatment. Cells were then exposed to drugs for 48 hours (72 hours for HepG2, U2OS, and 96 hours for MCF-7). After the drug-treatment, MTT (0.5 mg/ml) was added to cultures for an hour.
- % G ( TD ⁇ T 0/ TC ⁇ T 0) ⁇ 100 (1), where TC or TD represent O.D. readings of control or drug-treated cells.
- LC cytotoxicity
- This invention provides a composition effective in reducing or inhibiting cancer growth.
- the cancer includes but is not limited to bladder cancer, bone cancer and ovary cancer.
- This invention provides a composition comprising triterpenoidal saponins or their derivatives for inhibiting tumor growth.
- This invention provides a compound selected from a compound of formula (1):
- R1 and R2 represent angeloyl group
- R3 represents H or OH
- R4 represent CH2OR6
- R6 is H
- R5 represents at least one sugar moiety or its derivatives.
- R1 and R2 represent angeloyl group; R3 represents H or OH; R4 represents COOR6 wherein R6 is H.
- R1 represents H;
- R2 represents angeloyl group;
- R3 represents H or OH;
- R4 represents CH2OR6 or COOR6; wherein R6 is an angeloyl group.
- R4 represents CH2OR6 or COOR6; at least two of R1, R2, and R6 comprise an angeloyl group or acid having five carbons; R3 represents H or OH; and wherein R6 is angeloyl group, H, acetyl group, tigloyl group, senecioly group, or an acid having two to five carbons.
- At least one angeloyl of R1 or R2 is replaced by acetyl group, tigloyl group, senecioly group, or an acid having two to five carbons;
- R3 represents H or OH;
- R4 represents CH2OR6 or COOR6; and wherein R6 is angeloyl group.
- the R4 represents CH2OR6 or COOR6; and wherein R6 is H or acetyl.
- At least one of R1, R2, and R4 comprises a sugar moiety or is a compound comprises sugar moiety, wherein the sugar moiety comprises at least two angeloyl groups, acetyl group, tigloyl group, senecioly group, or an acid having two to five carbons or combination thereof.
- positions 23, 24, 25, 26, 29, 30 of the compound independently comprise CH3, CH2OH, CHO, COOH, alkyls group, acetyl group or derivative thereof.
- R5 represents sugar moiety comprising glucose, galactose or/and arabinose.
- R5 represents sugar moiety, wherein the sugar moiety comprises two sugars selected from D-glucose, D-galactose, L-rhamnose, L-arabinose, D-xylose, alduronic acid, D-glucuronic acid, D-galacturonic acid, and derivative thereof, and the combination thereof.
- R5 represents sugar moiety, wherein the sugar moiety comprises three sugars selected from D-glucose, D-galactose, L-rhamnose, L-arabinose, D-xylose, alduronic acid, D-glucuronic acid, D-galacturonic acid, and derivative thereof, and the combination thereof.
- R5 represents sugar moiety, wherein the sugar moiety comprises three sugars selected from D-glucose, D-galactose, L-rhamnose, L-arabinose, D-xylose, and derivative thereof, and the combination thereof.
- R5 represents sugar moiety, wherein the sugar moiety comprises at least one sugar, or D-glucose, D-galactose, or L-rhamnose, or L-arabinose, or D-xylose, or alduronic acid, or D-glucuronic acid or D-galacturonic acid, or derivative thereof, or the combination thereof.
- R5 represents a compound capable of performing the function of the sugar moiety.
- the R5 represents H.
- R4 represents H or OH or CH3.
- R1 or/and R2 is a functional group capable of performing the function of the angeloyl.
- R5 represents a compound capable of performing the function of the sugar moiety.
- a sugar moiety is a segment of molecule comprising one or more sugar group. Substitution, deletion and/or addition of any group in the above-described compounds will be apparent to one of ordinary skill in the art based on the teaching of this application. In a further embodiment, the substitution, deletion and/or addition of the group(s) in the compound of the invention does not substantially affect the biological function of the compound. In a further embodiment, the angeloyl groups are in a trans-position on a structure.
- This invention provides a compound selected from a compound of formula (2):
- R1 represents angeloyl group
- R2 represents angeloyl group
- R3 represents OH or H
- Positions 23, 24, 25, 26, 27, 29, of the compound independently comprise CH3, or CH2OH, or CHO, or COOH, alkyls group, or acetyl group, or derivative
- R6 represents Ac or H
- R5 represents sugar moiety, wherein the sugar moiety comprises at least one sugar, or D-glucose, or D-galactose, or L-rhamnose, or L-arabinose, or D-xylose, or alduronic acid, or D-glucuronic acid, or D-galacturonic acid, or their derivative thereof, or the combination thereof.
- R5 represents a compound capable of performing the function of the sugar moiety.
- the sugar moiety comprises L-arabinose, D-glucose and/or D-galactose, or combinations thereof.
- any two of R1, R2 or R6 are angeloyl groups, or any one of R1, R2 or R6 is attached to a sugar moiety in which two angeloyl groups are attached to adjacent carbons of the monosaccharides.
- R1, R2, and R6 comprises angeloyl group, acetyl group, tigloyl group, senecioly group, or an acid with two to five carbons or combination thereof.
- At least one of R1, R2 or R6 is attached a sugar moiety, wherein sugar moiety comprises two angeloyl group, acetyl group, tigloyl group, senecioly group, acid having two to five carbons, or combinations thereof.
- This invention provides a compound selected from a compound of formula (3):
- R1 represents angeloyl group
- R2 represents angeloyl group
- R3 represents OH or H
- R4 represents CH3 or CH2OH or alkyls group or their derivatives
- R6 represents Ac or H
- R5 represents sugar moiety, wherein the sugar moiety comprises at least one sugar, or D-glucose, or D-galactose, or L-rhamnose, or L-arabinose, or D-xylose, or alduronic acid, or D-glucuronic acid, or D-galacturonic acid, or derivative thereof, or the combination thereof.
- R5 represents a compound capable of performing the function of sugar moiety.
- the sugar moiety comprises L-arabinose, or D-glucose, or D-galactose, or combinations thereof.
- at least one of R1, R2 or R6 is attached a sugar moiety or rhamnose, wherein sugar moiety or rhamnose comprises two angeloyl group, acetyl group, tigloyl group, senecioly group, acid having two to five carbons, or combinations thereof.
- This invention provides a compound selected from a compound of formula (4):
- R1 and R2 represent angeloyl group
- R3 represents H or OH
- R4 represent CH2OR6
- R6 is H or acetyl
- R5 represents sugar moiety or D-glucose
- R7 represents a sugar moiety or L-arabinose
- R8 represents sugar moiety or D-galactose
- R9 represent COOH or CH2OH.
- R4 represents COOR6, wherein the R6 is H or acetyl.
- the R5, R7 or/and R8 are H or sugar moiety, wherein the sugar moiety comprises at least one sugar, or glucose, or galactose, or rhamnose, or arabinose, or xylose, or alduronic acid, or glucuronic acid or galacturonic acid, or derivative thereof.
- at least 2 of R1, R2 and R6 are angeloyl group;
- R4 represent CH2OR6 or COOR6, wherein R6, R1 and R2 are angeloyl group, acetyl group, tigloyl group, senecioly group, an acid having two to five carbons or H.
- R1, R2 and R6 are angeloyl group, acetyl group, tigloyl group, senecioly group, or an acid having two to five carbons;
- R3 represents H or OH;
- R4 represents CH2OR6 or COOR6, where R6 is H or angeloyl group, acetyl group, tigloyl group, senecioly group.
- R1 and R2 represent angeloyl group;
- R3 represents H or OH;
- R4 represents COOR6 wherein R6 is H;
- R1 represents H;
- R2 represents angeloyl group;
- R3 represents H or OH;
- R4 represents CH2OR6 or COOR6; wherein R6 is an angeloyl group.
- At least two of R1, R2, and R6 comprise an angeloyl group;
- R3 represents H or OH;
- R4 represents CH2OR6 or COOR6; and wherein R6 is H, angeloyl group, acetyl group, tigloyl group, senecioly group, or an acid having two to five carbons.
- At least one angeloyl of R1 or R2 is replaced by acetyl group, tigloyl group, senecioly group, or an acid having two to five carbons;
- R3 represents H or OH;
- R4 represents CH2OR6 or COOR6; and wherein R6 is angeloyl group.
- At least one of R1, R2, and R6 is a sugar moiety or rhamnose comprising at least two angeloyl groups, acetyl group, tigloyl group, senecioly group, or an acid having two to five carbons or combination thereof.
- positions 23, 24, 25, 26, 29, 30 of the compound independently comprise CH3, CH2OH, CHO, COOH, alkyls group, acetyl group or derivative thereof.
- R4 represents H or OH or CH3.
- a sugar moiety is a segment of molecule comprising one or more sugar group.
- This invention provides a compound selected from a compound of formula (5):
- R1 and R2 represent angeloyl group
- R3 represents H or OH
- R6 represent H or acetyl
- R9 represents COOH or CH2OH
- R10 represent CH3 or CH2OH or COOH
- R5, R7 and R8 are H or/and sugar moiety, wherein the sugar moiety comprises at least one sugar, D-glucose, D-galactose, L-rhamnose, L-arabinose, D-xylose, alduronic acid, D-glucuronic acid, or D-galacturonic acid, or derivative thereof.
- At least one of R1, R2, and R6 is a sugar moiety or compound comprising at least two angeloyl groups, acetyl group, tigloyl group, senecioly group, or an acid having two to five carbons or combination thereof. In another embodiment, at least two of R1, R2, and R6 comprise an angeloyl group
- This invention provides a compound selected from a compound of formula (6):
- R1 represents angeloyl group
- R2 represents angeloyl group
- R3 represents OH or H
- R4 represents CH3 or CH2OH
- R7 represents H
- R5 represents D-glucose, D-Galactose, L-arabinose or H
- R6 represents D-glucose, D-Galactose, L-arabinose or H.
- R5 or/and R6 are H or sugar moiety comprises at least one sugar, D-glucose, D-galactose, L-rhamnose, L-arabinose, D-xylose, alduronic acid, D-glucuronic acid, or D-galacturonic acid, or derivative thereof.
- a sugar moiety is a segment of molecule comprising one or more sugar group. Substitution, deletion and/or addition of any group in the above-described compounds will be apparent to one of ordinary skill in the art based on the teaching of this application. In a further embodiment, the substitution, deletion and/or addition of the group(s) in the compound of the invention does not substantially affect the biological function of the compound.
- This invention provides a compound selected from a compound of formula (1A):
- R1 and R2 independently represent angeloyl group
- R3 represents H or OH
- R4 represent CH2OR6
- R6 is H
- R5 represents at least one sugar moiety or its derivatives.
- R1 and R2 independently represent angeloyl group; R3 represents H or OH; R4 represents COOR6 wherein R6 is H; R5 represents at least one sugar moiety or its derivatives.
- R1 represents H;
- R2 represents angeloyl group;
- R3 represents H or OH;
- R4 represents CH2OR6 or COOR6; wherein R6 is an angeloyl group; and
- R5 represents at least one sugar moiety or its derivatives.
- R3 represents H or OH
- R4 represents CH2OR6 or COOR6
- R6 is angeloyl group, H, acetyl group, tigloyl group, senecioyl group, or an acid having two to five carbons
- at least two of R1, R2, and R6 comprise an angeloyl group or acid having five carbons
- R5 represents at least one sugar moiety or its derivatives.
- At least one angeloyl from R1 or R2 is replaced by acetyl group, tigloyl group, senecioyl group, or an acid having two to five carbons;
- R3 represents H or OH;
- R4 represents CH2OR6 or COOR6 wherein R6 is angeloyl group;
- R5 represents at least one sugar moiety or its derivatives.
- R4 represents CH2OR6 or COOR6; at least one of R1, R2, and R6 is a sugar moiety comprising at least two angeloyl groups, acetyl group, tigloyl group, senecioyl group, or an acid having two to five carbons or combination thereof.
- position 24 of the compound comprises CH3 or CH2OH.
- positions 23, 24, 25, 26, 29, 30 of the compound independently comprise CH3 or CH2OH.
- positions 23, 24, 25, 26, 29, 30 of the compound independently comprise CH3, CH2OH, CHO, COOH, COOalkyl, COOaryl, COO-heterocyclic, COO-heteroaryl, CH 2 Oaryl, CH 2 O-heterocyclic, CH 2 O-heteroaryl, alkyls group, acetyl group or derivative thereof.
- R5 represents sugar moiety comprising glucose, galactose and arabinose.
- R5 represents sugar moiety, wherein the sugar moiety comprises at least one sugar, or D-glucose, D-galactose, or L-rhamnose, or L-arabinose, or D-xylose, or alduronic acid, or D-glucuronic acid or D-galacturonic acid, or derivative thereof, or the combination thereof.
- R5 represents sugar moiety, wherein the sugar moiety comprises two sugars comprising D-glucose, or D-galactose, or L-rhamnose, or L-arabinose, or D-xylose, or alduronic acid, or D-glucuronic acid or D-galacturonic acid, or derivative thereof, or the combination thereof.
- R5 represents sugar moiety, wherein the sugar moiety comprises at least three sugars selected from D-glucose, or D-galactose, or L-rhamnose, or L-arabinose, or D-xylose, or alduronic acid, or D-glucuronic acid or D-galacturonic acid, or derivative thereof, or the combination thereof.
- R5 represents sugar moiety, wherein the sugar moiety comprises at least one sugar, glucose, galactose, rhamnose, arabinose, xylose, fucose, allose, altrose, gulose, idose, lyxose, mannose, psicose, ribose, sorbose, tagatose, talose, fructose, alduronic acid, glucuronic acid or galacturonic acid, or derivative thereof, or the combination thereof.
- R5 represents sugar moiety, wherein the sugar moiety comprises three sugars selected from glucose, galactose, rhamnose, arabinose, xylose, fucose, allose, altrose, gulose, idose, lyxose, mannose, psicose, ribose, sorbose, tagatose, talose, fructose, alduronic acid, glucuronic acid and galacturonic acid, and derivative thereof, and the combination thereof.
- sugar moiety comprises three sugars selected from glucose, galactose, rhamnose, arabinose, xylose, fucose, allose, altrose, gulose, idose, lyxose, mannose, psicose, ribose, sorbose, tagatose, talose, fructose, alduronic acid, glucuronic acid and galacturonic acid, and derivative thereof, and the combination thereof.
- R5 represents sugar moiety, wherein the sugar moiety comprises three sugars selected from glucose, galactose, rhamnose, arabinose, xylose, fucose, and derivative thereof, and the combination thereof.
- R5 represents a compound capable of performing the function of the sugar moiety.
- the R5 represents H.
- R4 represents H or OH or CH3.
- R1 or/and R2 is a functional group capable of performing the function of the angeloyl.
- R5 represents a compound capable of performing the function of the sugar moiety.
- R1 and R2 are selected from angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, dibenzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl.
- R1 and R2 comprise angeloyl, tigloyl, senecioyl, benzoyl or alkenoyl.
- R4 represents CH2OR6; at least two of R1, R2 and R6 are selected from angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, dibenzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl.
- R4 represents CH2OR6; at least two of R1, R2 and R6 are comprise angeloyl, tigloyl, senecioyl, benzoyl or alkenoyl.
- R4 represents CH2OR6; at least two of R1, R2 and R6 are comprise angeloyl, benzoyl or alkenoyl.
- R1 and R2 are selected from H, angeloyl, acetyl, tigloyl, senecioyl, alkyl, acyl, benzoyl, dibenzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, heterocylic or heteroraryl;
- R4 represents CH2OR6 or COOR6; wherein R6 is selected from H, COCH3, angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, dibenzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl or derivative thereof.
- R4 represents CH2OR6, COOR6 or CH2COOR6; at least two of R1, R2 and R6 are selected from angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, dibenzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl or derivative thereof.
- At least two of R1, R2 and R4 are comprising angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, dibenzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl or derivative thereof.
- At least two of R1, R2 and R4 comprise angeloyl, acetyl, tigloyl, senecioyl, benzoyl, alkenoyl, or derivative thereof.
- At least two of R1, R2 and R4 comprise angeloyl, tigloyl, senecioyl, benzoyl, alkenoyl, or derivative thereof.
- At least two of R1, R2 and R4 comprise a compound capable of performing the function of angeloyl.
- At least two of R1, R2 and R4 comprise a compound capable of performing the function of benzoyl.
- R4 represents CH2OR6, COOR6 or CH2COOR6; at least two of R1, R2 and R6 are comprise angeloyl, tigloyl, senecioyl, benzoyl, alkenoyl, benzoyl or derivative thereof.
- R4 represents CH2OR6, COOR6 or CH2COOR6;
- R1, R2 and/or R6 is/are sugar moiety, which comprise compounds selected from H, angeloyl, acetyl, tigloyl, senecioly, alkyl, benzoyl, dibenzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl or derivative thereof.
- R4 represents CH2OR6, COOR6 or CH2COOR6;
- R1, R2 and/or R6 is/are sugar moiety, which comprise at least 2 compounds selected from angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, dibenzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl or derivative thereof.
- R4 represents CH2OR6, COOR6 or CH2COOR6;
- R1, R2 and/or R6 is/are sugar moiety, which comprise at least 2 compounds selected from angeloyl, tigloyl, senecioyl, benzoyl, alkenoyl or derivative thereof.
- R4 represents CH2OR6, COOR6 or CH2COOR6;
- R1, R2 and/or R6 is/are sugar moiety, which comprise at least 2 compounds selected from angeloyl, benzoyl, alkenoyl or derivative thereof.
- a compound selected from formula (1A) comprises at least 2 compounds selected from angeloyl, acetyl, tigloyl, senecioyl, or derivative thereof or a compound capable performing the function of angeloyl.
- a compound selected from formula (1A) comprise at least 2 compounds selected from angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, dibenzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl or derivative thereof.
- a compound selected from formula (1A) comprises a sugar moiety or a compound capable of performing function of sugar moiety and at least 2 compounds selected from angeloyl, acetyl, tigloyl, senecioyl, or derivative thereof or a compound capable performing the function of angeloyl.
- a compound selected from formula (1A) comprise a sugar moiety or a compound capable of performing the function of sugar moiety and at least 2 compounds selected from angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, dibenzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl or derivative thereof.
- R4 is a compound comprising CH2OCCH3, CH2COOalkyl, CH2OH, COOH, angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, dibenzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl or derivative thereof.
- a sugar moiety is a segment of molecule comprising one or more sugar group. Substitution, deletion and/or addition of any group in the above-described compounds will be apparent to one of ordinary skill in the art based on the teaching of this application. In a further embodiment, the substitution, deletion and/or addition of the group(s) in the compound of the invention does not substantially affect the biological function of the compound.
- This invention provides a compound selected from a compound of formula (1B):
- R1 comprise compound selected from hydrogen, angeloyl, acetyl, tigloyl, senecioyl, alkyl, dibenzoyl, benzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, heterocylic or heteroraryl or derivative thereof;
- R2 comprise compound selected from hydrogen, angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, dibenzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl or derivative thereof;
- R4 represents CH2OR6, COOR6 wherein R6 is selected from hydrogen, angeloyl, acetyl, tigloyl, senecioyl, alkyl, dibenzoyl
- R1 represent a sugar moiety comprises at least two compound selected from, angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, dibenzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl or derivative thereof.
- R2 represent a sugar moiety comprises at least one compound selected from, angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, dibenzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl or derivative thereof.
- R2 represent a sugar moiety or a compound comprises at least two compound selected from, angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, dibenzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl or derivative thereof.
- R4 represents CH2OR6, COOR6 wherein R6 is a sugar moiety which comprises at least one compound selected from angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, dibenzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl or derivative thereof.
- R6 is a sugar moiety which comprises at least one compound selected from angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, dibenzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl or derivative thereof.
- R4 represents CH2OR6, COOR6 wherein R6 is a sugar moiety which comprises at least two compounds selected from angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, dibenzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl or derivative thereof.
- R6 is a sugar moiety which comprises at least two compounds selected from angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, dibenzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl or derivative thereof.
- R4 represents CH2OR6, COOR6 wherein R6 is a sugar moiety which comprises at least two compounds selected from angeloyl, acetyl, tigloyl, senecioyl, alkyl,
- R4 represents CH2OR6, COOR6 wherein R6 is a sugar moiety which comprises at least two compounds selected from angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, dibenzoyl, alkanoyl, alkenoyl, dibenzoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl or derivative thereof.
- R6 is a sugar moiety which comprises at least two compounds selected from angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, dibenzoyl, alkanoyl, alkenoyl, dibenzoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl or derivative thereof.
- R4 represents CH2OR6, COOR6 of formula (1B), at least two of R1, R2 and R6 comprise the compound selected from angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, dibenzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl or derivative thereof.
- R4 represents CH2OR6, COOR6 of formula (1B), at least two of R1, R2 and R6 comprise angeloyl, benzoyl, alkenoyl, or derivative thereof.
- R4 is a compound comprising CH2OCCH3, CH2COOalkyl, CH2OH, COOH, angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, dibenzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl or derivative thereof.
- R5 represents sugar moiety, wherein the sugar moiety comprises at least one sugar, glucose, galactose, rhamnose, arabinose, xylose, fucose, allose, altrose, gulose, idose, lyxose, mannose, psicose, ribose, sorbose, tagatose, talose, fructose, alduronic acid, glucuronic acid or galacturonic acid, or derivative thereof, or the combination thereof.
- R5 represents sugar moiety, wherein the sugar moiety comprises two sugars selected from glucose, galactose, rhamnose, arabinose, xylose, fucose, allose, altrose, gulose, idose, lyxose, mannose, psicose, ribose, sorbose, tagatose, talose, fructose, alduronic acid, glucuronic acid, galacturonic acid, and derivative thereof, and the combination thereof.
- the sugar moiety comprises two sugars selected from glucose, galactose, rhamnose, arabinose, xylose, fucose, allose, altrose, gulose, idose, lyxose, mannose, psicose, ribose, sorbose, tagatose, talose, fructose, alduronic acid, glucuronic acid, galacturonic acid, and derivative thereof, and the combination thereof
- R5 represents sugar moiety, wherein the sugar moiety comprises three sugars selected from glucose, galactose, rhamnose, arabinose, xylose, fucose, allose, altrose, gulose, idose, lyxose, mannose, psicose, ribose, sorbose, tagatose, talose, fructose, alduronic acid, glucuronic acid, galacturonic acid, and derivative thereof, and the combination thereof.
- sugar moiety comprises three sugars selected from glucose, galactose, rhamnose, arabinose, xylose, fucose, allose, altrose, gulose, idose, lyxose, mannose, psicose, ribose, sorbose, tagatose, talose, fructose, alduronic acid, glucuronic acid, galacturonic acid, and derivative thereof, and the combination thereof.
- R5 represents sugar moiety, wherein the sugar moiety comprises at least four sugars selected from glucose, galactose, rhamnose, arabinose, xylose, fucose, allose, altrose, gulose, idose, lyxose, mannose, psicose, ribose, sorbose, tagatose, talose, fructose, alduronic acid, glucuronic acid, galacturonic acid, and derivative thereof, and the combination thereof.
- sugar moiety comprises at least four sugars selected from glucose, galactose, rhamnose, arabinose, xylose, fucose, allose, altrose, gulose, idose, lyxose, mannose, psicose, ribose, sorbose, tagatose, talose, fructose, alduronic acid, glucuronic acid, galacturonic acid, and derivative thereof, and
- R5 represents sugar moiety, wherein the sugar moiety comprises three sugars selected from glucose, galactose, rhamnose, arabinose, xylose, fucose, and derivative thereof, and the combination thereof.
- R5 represents sugar moiety or a compound capable of performing the function of the sugar moiety.
- the R5 represents H.
- R4 represents H or OH or CH3.
- positions 23, 24, 25, 26, 29, 30 of the compound independently comprise CH3, CH2OH, CHO, COOH, COOalkyl, COOaryl, COO-heterocyclic, COO-heteroaryl, CH 2 Oaryl, CH 2 O-heterocyclic, CH 2 O-heteroaryl, alkyls group, acetyl group or derivative thereof.
- R5 represents sugar moiety selected from D-glucose, D-galactose, L-rhamnose and L-arabinose and their combination thereof.
- R5 represents sugar moiety comprising D-glucose, D-galactose and L-arabinose or their combination thereof.
- R5 represents sugar moiety comprising D-glucose, D-galactose, L-rhamnose, D-xylose or L-arabinose or their combination thereof or derivative thereof.
- R5 represents sugar moiety, wherein the sugar moiety comprises at least two sugar selected from D-glucose, D-galactose, L-rhamnose, L-arabinose, D-xylose, alduronic acid, D-glucuronic acid, D-galacturonic acid and derivative thereof, and the combination thereof.
- R5 represents sugar moiety, wherein the sugar moiety comprises three sugars selected from D-glucose, D-galactose, L-rhamnose, L-arabinose, D-xylose, alduronic acid, D-glucuronic acid, D-galacturonic acid and derivative thereof, and the combination thereof.
- R5 represents sugar moiety, wherein the sugar moiety comprises at least three sugars selected from D-glucose, D-galactose, L-rhamnose, L-arabinose, D-xylose, alduronic acid, D-glucuronic acid, D-galacturonic acid and derivative thereof, and the combination thereof.
- R1 and R2 independently comprise an angeloyl group.
- R1 is a sugar moiety or a compound which comprise two angeloyl groups.
- R1 and R2 independently comprise a benzoyl group.
- R1 is a sugar moiety which comprises two benzoyl groups.
- R3 represents H or OH.
- a sugar moiety is a segment of molecule comprising one or more sugar group. Substitution, deletion and/or addition of any group in the above-described compounds will be apparent to one of ordinary skill in the art based on the teaching of this application. In a further embodiment, the substitution, deletion and/or addition of the group(s) in the compound of the invention does not substantially affect the biological function of the compound.
- This invention provides a compound selected from a compound of formula (1C):
- R1 and R2 independently represent angeloyl group
- R3 represents H or OH
- R4 represent CH2OR6 wherein R6 is H
- R5 represents sugar moiety or D-glucose, D-galactose or its derivatives.
- R7 represent COOH
- R1 and R2 independently represent angeloyl group;
- R3 represents H or OH;
- R4 represents COOR6 wherein R6 is H;
- R5 represents sugar moiety or D-glucose, D-galactose or its derivatives.
- R7 represent COOH.
- R1 represents H;
- R2 represents angeloyl group;
- R3 represents H or OH;
- R4 represents CH2OR6 or COOR6; wherein R6 is an angeloyl group or acetyl group.
- At least two of R1, R2, and R6 comprise an angeloyl group or acid having five carbons;
- R3 represents H or OH;
- R4 represents CH2OR6 or COOR6; and wherein R6 is angeloyl group, H, acetyl group, tigloyl group, senecioyl group, or an acid having two to five carbons.
- At least one angeloyl from R1 or R2 is replaced by acetyl group, tigloyl group, senecioyl group, or an acid having two to five carbons;
- R3 represents H or OH;
- R4 represents CH2OR6 or COOR6 wherein R6 is angeloyl group.
- R4 represents CH2OR6 or COOR6; at least one of R1, R2, and R6 is a sugar moiety comprising at least two angeloyl groups, acetyl group, tigloyl group, senecioyl group, or an acid having two to five carbons or combination thereof.
- positions 24 of the compound comprise CH3 or CH2OH.
- R7 represent COOH, CH2OH or CH3.
- R7 represent CH3, CH2OH, CHO, COOH, COOalkyl.
- R7 represent CH3, CH2OH, CHO; COOH, COOalkyl, COOaryl, COO-heterocyclic, COO-heteroaryl, CH 2 Oaryl, CH 2 O-heterocyclic, CH 2 O-heteroaryl, alkyls group, acetyl group or derivative thereof.
- positions 24 of the compound comprise CH3 or CH2OH.
- positions 23, 24, 25, 26, 29, 30 of the compound independently comprise CH3, CH2OH.
- positions 23, 24, 25, 26, 29, 30 of the compound independently comprise CH3, CH2OH, CHO, COOH, COOalkyl, COOaryl, COO-heterocyclic, COO-heteroaryl, CH 2 Oaryl, CH 2 O-heterocyclic, CH 2 O-heteroaryl, alkyls group, acetyl group or derivative thereof.
- R5 represents sugar moiety comprising glucose or galactose.
- R5 represents sugar moiety, or D-glucose, D-galactose, or L-rhamnose, or L-arabinose, or D-xylose, or alduronic acid, or D-glucuronic acid or D-galacturonic acid, or derivative thereof, or the combination thereof.
- R5 represents sugar moiety, glucose, galactose, rhamnose, arabinose, xylose, fucose or derivative thereof.
- R5 represents sugar moiety, glucose, galactose, rhamnose, arabinose, xylose, fucose, allose, altrose, gulose, idose, lyxose, mannose, psicose, ribose, sorbose, tagatose, talose, fructose, alduronic acid, glucuronic acid or galacturonic acid, or derivative thereof, or the combination thereof.
- the R5 represents H.
- R4 represents CH2OR6 wherein R6 represent H or acetyl group.
- R4 represents H or OH or CH3.
- R1 or/and R2 is a functional group capable of performing the function of the angeloyl.
- R5 represents a compound capable of performing the function of the sugar moiety.
- R1 and R2 are selected from angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl or derivative thereof.
- R1 or/and R2 is a sugar moiety comprise two of compounds selected from angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl or derivative thereof.
- R1 and R2 are selected from H, angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl;
- R4 represents CH2OR6 or COOR6; wherein R6 is selected from H, COCH3, angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl or derivative thereof.
- R4 represents CH2OR6, COOR6 or CH2COOR6; at least two of R1, R2 and R6 are selected from angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl or derivative thereof.
- R4 represents CH2OR6, COOR6 or CH2COOR6;
- R1, R2 and/or R6 is/are sugar moiety, which comprise compounds selected from H angeloyl, acetyl, tigloyl, senecioly, alkyl, benzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl or derivative thereof.
- R4 represents CH2OR6, COOR6 or CH2COOR6;
- R1, R2 and/or R6 is/are sugar moiety, which comprise at least 2 compounds selected from angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl or derivative thereof.
- a compound selected from formula (1C) comprises at least 2 compounds selected from angeloyl, acetyl, tigloyl, senecioyl, or derivative thereof or a compound capable performing the function of angeloyl.
- a compound selected from formula (1C) comprise at least 2 compounds selected from angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl or derivative thereof.
- R4 is a compound comprising CH2OCCH3, CH2COOalkyl, CH2OH, COOH, angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl or derivative thereof.
- a sugar moiety is a segment of molecule comprising one or more sugar group.
- substitution, deletion and/or addition of any group in the above-described compounds will be apparent to one of ordinary skill in the art based on the teaching of this application.
- substitution, deletion and/or addition of the group(s) in the compound of the invention does not substantially affect the biological function of the compound.
- This invention provides a compound selected from a compound of formula (1D):
- R1 comprise compound selected from hydrogen, angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl or derivative thereof;
- R2 comprise compound selected from hydrogen, angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl or derivative thereof;
- R4 represents CH2OR6, COOR6 wherein R6 is selected from hydrogen, angeloyl, acetyl, tigloyl, senecioyl, alkyl,
- R7 represent CH3, CH2OH, COOH, COOalkyl
- R7 represent CH3, CH2OH, CHO, COOH, COOalkyl, COOaryl, COO-heterocyclic, COO-heteroaryl, CH 2 Oaryl, CH 2 O-heterocyclic, CH 2 O-heteroaryl, alkyls group, acetyl group or derivative thereof.
- R1 represent a compound comprising a sugar moiety comprises at least two compound selected from, angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl or derivative thereof;
- R1 represent a compound comprising a sugar moiety comprises at least one compound selected from, angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl or derivative thereof;
- R2 represent a compound comprising a sugar moiety comprises at least one compound selected from, angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl or derivative thereof;
- R2 represent a compound comprising a sugar moiety or a compound which comprises at least two compound selected from, angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl or derivative thereof;
- R4 represents CH2OR6, COOR6 wherein R6 is a sugar moiety which comprises at least one compound selected from angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl or derivative thereof;
- R4 represents CH2OR6, COOR6 wherein R6 is a sugar moiety which comprises at least two compounds selected from angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl or derivative thereof;
- R4 represents CH2OR6, COOR6 wherein R6 is a sugar moiety which comprises at least two compounds selected from angeloyl, acetyl, tigloyl, senecioyl, alkyl,
- R4 represents CH2OR6, COOR6 wherein R6 is a sugar moiety which comprises at least two compounds selected from angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, alkanoyl, alkenoyl, dibenzoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl or derivative thereof;
- R4 represents CH2OR6, COOR6 wherein at least two of R1, R2 and R6 comprise the compound selected from angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl or derivative thereof;
- R4 is a compound comprising CH2OCCH3, CH2COOalkyl, CH2OH, COOH, angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl or derivative thereof.
- R5 represents sugar moiety, glucose, galactose, rhamnose, arabinose, xylose, fucose, allose, altrose, gulose, idose, lyxose, mannose, psicose, ribose, sorbose, tagatose, talose, fructose, alduronic acid, glucuronic acid or galacturonic acid, or derivative thereof, or the combination thereof.
- R5 represents a compound capable of performing the function of the sugar moiety.
- the R5 represents H.
- R4 represents H or OH or CH3.
- position 24 of the compound comprise CH3 or CH2OH
- positions 23, 24, 25, 26, 29, 30 of the compound independently comprise CH3, CH2OH, CHO, COOH, COOalkyl, COOaryl, COO-heterocyclic, COO-heteroaryl, CH 2 Oaryl, CH 2 O-heterocyclic, CH 2 O-heteroaryl, alkyls group, acetyl group or derivative thereof.
- R5 represents sugar moiety comprising L-glucose, D-galactose, L-rhamnose, or/and L-arabinose.
- R1 and R2 independently represent angeloyl group; In a further embodiment, R1 is a sugar moiety or rhamnose which comprise two angeloyl groups.
- R3 represents H or OH
- a sugar moiety is a segment of molecule comprising one or more sugar group. Substitution, deletion and/or addition of any group in the above-described compounds will be apparent to one of ordinary skill in the art based on the teaching of this application. In a further embodiment, the substitution, deletion and/or addition of the group(s) in the compound of the invention does not substantially affect the biological function of the compound.
- This invention provides a method of inhibiting tumor cell growth comprising administering to a subject, in need thereof, an appropriate amount of triterpenoidal saponins comprising two or more angeloyl groups or comprising the structure of FIGS. 1-27 .
- This invention provides a composition comprising the compounds as described above effective in reducing or inhibiting cancer growth.
- the cancer includes but is not limited to bladder cancer, bone cancer, skin cancer and ovarian cancer.
- the saponins isolated from Xanthoceras sorbifolia with the characteristic structure described in the present invention can be used for anti-cancer therapy.
- the cancer includes but is not limited to bladder cancer, bone cancer, skin cancer and ovarian cancer.
- This invention provides a composition comprising the above described compounds or their derivatives for treating human immunodeficiency virus (HIV), Severe Acute Respiratory Syndrome (SARS), flu disease or inhibits virus activities.
- HIV human immunodeficiency virus
- SARS Severe Acute Respiratory Syndrome
- flu disease or inhibits virus activities.
- the biologically active triterpenoid saponins structures are shown in FIG. 1
- Triterpenoid saponins comprises the formula as following:
- This invention provides a composition comprising the compounds as described above effective in reducing or inhibiting cancer growth.
- the cancer includes but is not limited to bladder cancer, bone, cancer, skin cancer and ovarian cancer.
- composition for reducing or inhibiting cancer growth comprising any of compound selected from following:
- composition for reducing or inhibiting cancer growth comprising any of compound selected from following:
- Triterpenoid saponins with the characteristic structure mentioned above in this invention can be used to reduce or inhibit cancer growth.
- the cancer includes but is not limited to bladder cancer, bone cancer, skin cancer and ovarian cancer.
- This invention also provides a composition comprising the above described compounds or their derivatives capable of inhibiting human immunodeficiency virus (HIV), Severe Acute Respiratory Syndrome (SARS) or flu disease, or capable of inhibiting viral activities.
- HIV human immunodeficiency virus
- SARS Severe Acute Respiratory Syndrome
- flu disease or capable of inhibiting viral activities.
- the saponins isolated from Harpullia austro - calcdonica with the characteristic structure described in the present invention can be used for anti-cancer therapy.
- the cancer includes but is not limited to bladder cancer, bone cancer and ovarian cancer.
- This invention provides a composition comprising the above described compounds or their derivatives for inhibiting human immunodeficiency virus (HIV), Severe Acute Respiratory Syndrome (SARS), flu disease or inhibits virus activities.
- HAV human immunodeficiency virus
- SARS Severe Acute Respiratory Syndrome
- FIG. 11A The biologically active triterpenoid saponins structures are shown in FIG. 11A . See also Phytochemistry 59 (2002) 825-832, Triterpenoid saponins and acylated prosapogenins from Harpullia austro - calcdonica.
- R3 CH2OH or CH3 or CHO.
- the biologically active triterpenoid saponins structures are shown in FIG. 15 . See also Phytochemistry 66 (2005) 825-835, Haemolytic acylated triterpenoid saponins from Harpullia austro - caledonica.
- Triterpenoid saponins isolated from seeds of Aesculus chinensis having the characteristic structure(s) as disclosed in the present invention can be used in anti-cancer therapy.
- the cancer that triterpenoid saponins is effective against includes but is not limited to bladder cancer, bone cancer and ovarian cancer.
- This invention provides a composition comprising the above-described compounds and their derivatives for inhibiting cancer, Severe Acute Respiratory Syndrome (SARS), flu disease or inhibits virus activities.
- SARS Severe Acute Respiratory Syndrome
- Triterpenoidal saponins comprise the structures shown or described in FIG. 7A .
- R1 R2 R3 1 Tigloyl Acetyl H 2 Angeloyl Acetyl H 3 Tigloyl H H 4 Angeloyl H Acetyl 5 H Tigloyl Acetyl 6 H Angeloyl Acetyl 7 H H Tigloyl 8 H H Angeloyl
- Aesculus glabra Willd. Aesculus hippocastanum, Aesculus indica, Aesculus lantsangensis Hu et Fang, wangii Aesculus megaphylla Hu et Fang, chinensis Aesculus neglecta, Aesculus octandra Marsh., Aesculus parvifiora, Aesculus pavia, Aesculus polyneura Hu et Fang, Aesculus tsianguii Hu et Fang, Aesculus sylvatica, Aesculus turbinata, Aesculus wangii Hu, Aesculus wangii var.
- ruticola Hu et Fang or Aesculus wilsonii having the characteristic structure(s) as disclosed in the present invention can be used in anti-cancer therapy.
- the cancer that triterpenoid saponin is effective against includes but is not limited to bladder cancer, bone cancer and ovarian cancer.
- This invention provides a composition comprising the above-described compounds and their derivatives for inhibiting cancer, Severe Acute Respiratory Syndrome (SARS), flu disease or inhibits virus activities.
- SARS Severe Acute Respiratory Syndrome
- Triterpenoid saponins comprise the structures shown or described in FIG. 7A , 7 B, 7 C, 7 D.
- Position 23-27 and 28-30 are attached with CH3 or CH2OH or COOH or CHO
- Aesculus glabra Willd. Aesculus hippocastanum, Aesculus indica, Aesculus lantsangensis Hu et Fang, wangii Aesculus megaphylla Hu et Fang, chinensis Aesculus neglecta, Aesculus octandra Marsh., Aesculus parviflora, Aesculus pavia, Aesculus polyneura Hu et Fang, Aesculus tsianguii Hu et Fang, Aesculus sylvatica, Aesculus turbinata, Aesculus wangii Hu, Aesculus wangii var.
- ruticola Hu et Fang or Aesculus wilsonii having the characteristic structure(s) as disclosed in the present invention can be used in anti-cancer therapy.
- the cancer that triterpenoid saponin is effective against includes but is not limited to bladder cancer, bone cancer, skin cancer and ovarian cancer.
- This invention provides a composition comprising the above-described compounds and their derivatives for inhibiting cancer, Severe Acute Respiratory Syndrome (SARS), flu disease or inhibits virus activities.
- SARS Severe Acute Respiratory Syndrome
- Triterpenoidal saponins comprise the structures shown or described in FIG. 16A , 16 B.
- Triterpenoid saponins isolated from the plants described in this invention with the characteristic structure mentioned in this invention can be used to reduce or inhibit cancer growth.
- the cancer includes but is not limited to bladder cancer, bone cancer, skin cancer and ovarian cancer.
- This invention also provides a composition comprising the above described compounds or their derivatives capable of inhibiting human immunodeficiency virus (HIV), Severe Acute Respiratory Syndrome (SARS) or flu disease, or capable of inhibiting viral activities.
- HIV human immunodeficiency virus
- SARS Severe Acute Respiratory Syndrome
- flu disease or capable of inhibiting viral activities.
- Triterpenoid saponins isolated from roots of Camellia sinensis var. assamica , showed in FIG. 13 with the characteristic structure mentioned in this invention is effective in inhibiting or reducing cancer growth.
- the cancer includes but is not limited to bladder cancer, bone cancer, skin cancer and ovarian cancer.
- This invention provides a composition comprising the above described compounds and their derivatives for inhibiting human immunodeficiency virus (HIV), Severe Acute Respiratory Syndrome (SARS), flu disease or inhibits virus activities. See also Phytochemistry 53 (2000) 941-946 Triterpenoid saponins from the roots of tea plant ( Camellia sinensis var. assamica ).
- Triterpenoid saponins isolated from Pittosporum viridiflorum with the characteristic structure mentioned in this invention can be used to reduce or inhibit cancer growth.
- the cancer includes but is not limited to bladder cancer, bone cancer, skin cancer and ovarian cancer.
- This invention also provides a composition comprising the above described compounds or their derivatives capable of inhibiting human immunodeficiency virus (HIV), Severe Acute Respiratory Syndrome (SARS) or flu disease, or capable of inhibiting viral activities.
- HIV human immunodeficiency virus
- SARS Severe Acute Respiratory Syndrome
- flu disease or capable of inhibiting viral activities.
- the triterpenoid saponins isolated from Pittosporum tobira with the characteristic structure mentioned in this invention can be used for anti-cancer therapy.
- the cancer includes but is not limited to bladder cancer, bone cancer and ovary cancer.
- This invention also provides a composition comprising the above described compounds and their derivatives capable of inhibiting human immunodeficiency virus (HIV), Severe Acute Respiratory Syndrome (SARS) or flu disease, or capable of inhibiting viral activities.
- HIV human immunodeficiency virus
- SARS Severe Acute Respiratory Syndrome
- the triterpenoid saponins isolated from Maesa lanceolata with the characterized structure mentioned in this invention can be used to reduce or inhibit cancer growth.
- the cancer includes but is not limited to bladder cancer, bone cancer and ovarian cancer.
- This invention also provides a composition comprising the above described compounds or their derivatives capable of inhibiting human immunodeficiency virus (HIV), Severe Acute Respiratory Syndrome (SARS) or flu disease, or capable of inhibiting viral activities.
- HIV human immunodeficiency virus
- SARS Severe Acute Respiratory Syndrome
- flu disease or capable of inhibiting viral activities.
- the triterpenoid saponins isolated from Xanthoceras sobifolia with the characteristic structure mentioned in this invention can be used to reduce or inhibit cancer growth.
- the cancer includes but is not limited to bladder cancer, bone cancer and ovarian cancer.
- This invention also provides a composition comprising the above described compounds or their derivatives capable of inhibiting human immunodeficiency virus (HIV), Severe Acute Respiratory Syndrome (SARS) or flu disease, or capable of inhibiting viral activities.
- HIV human immunodeficiency virus
- SARS Severe Acute Respiratory Syndrome
- This invention provides a method for inhibiting tumor cell growth, human immunodeficiency virus (HIV), Severe Acute Respiratory Syndrome (SARS) or flu disease, or capable of inhibiting viral activities, comprising contacting an effective amount of the compounds in FIG. 1 to FIG. 27 .
- the above described compound comprising at least two angeloyl groups at carbon 21, 22 and 28.
- the above described compound comprising at least two angeloyl groups, tigloyl groups, senecioyl groups or acetyl group or their combinations.
- This invention provides a method for inhibiting tumor cell growth, human immunodeficiency virus (HIV), Severe Acute Respiratory Syndrome (SARS) or flu disease, or capable of inhibiting viral activities, comprising contacting an effective amount of the compounds in the FIGS. 3A and B wherein the compound comprises two angeloyl groups at any two of R1, R2 and R4; or the compounds in FIGS. 5A , 5 B, 6 A and 6 B wherein the compound comprises two angeloyl groups at any two of R1, R2, R3 and R4; or the compounds in FIGS. 7A , 7 B, 7 C and 7 D wherein the compound comprises two angeloyl groups at any two of R1, R2 and R3; or the compounds in FIG.
- HCV human immunodeficiency virus
- SARS Severe Acute Respiratory Syndrome
- the compound comprises two angeloyl groups at any two of R1, R2 and R3; or the compounds in FIGS. 9A , 9 B and 10 wherein the compound comprises two angeloyl groups at any two of R1, R2 and R3; or the compounds in FIGS. 11 , 12 and 13 wherein the compound comprises angeloyl groups at R1 and R2; or the compounds in FIG. 14 wherein the compound comprises two angeloyl groups at any two of R1, R2 and R3; or the compounds in FIG. 15 wherein the compound comprises two angeloyl groups; or the compounds in FIG. 16 wherein the compound comprises two angeloyl groups at any two of R1, R2 and R6; or the compounds in FIG. 16-25 wherein the compound comprises two angeloyl groups.
- This invention provides a method for inhibiting tumor cell growth, human immunodeficiency virus (HIV), Severe Acute Respiratory Syndrome (SARS) or flu disease, or capable of inhibiting viral activities, comprising contacting an effective amount of the above described compounds.
- the compound is a triterpenoidal saponin or a sapongenin comprising two angeloyl groups attached to carbon 21 and 22 of its sapogenin.
- the sapongenin comprising any two of angeloyl groups, tigloyl groups or senecioyl groups, or their combinations thereof attached to carbon 21 and 22 of its sapogenin.
- the compound is a triterpenoidal saponin or a sapongenin comprising any two of angeloyl groups, tigeloyl groups or senecioyl groups, or their combinations thereof attached to a sugar moiety which bonds to carbon 21 or 22.
- the compound is a triterpenoidal saponin or sapongenin comprising at least any one of angeloyl group, tigloyl group, or senecioyl group, or their combinations thereof attached to carbon 21 and/or 22 of its sapogenin.
- the compound is a triterpenoidal saponin or a sapongenin comprising at least two of angeloyl group or tigloyl group or senecioyl group, or their combinations thereof attached to a sugar moiety which bonds to carbon 21 or 22.
- the compound is a triterpenoidal saponin or a sapongenin comprising at least two angeloyl groups attached to carbon 21, 22 or 28 of its sapogenin.
- the compound is a triterpenoidal saponin or a sapongenin comprising any two of angeloyl groups, tigeloyl groups or senecioyl groups, or their combinations thereof attached to a sugar moiety which bonds to carbon 21, 22 or 28.
- the compound is a triterpenoidal saponin or a sapongenin comprising a sugar moiety comprises at least two angeloyl groups attached to carbon 21, 22 or 28 of its sapogenin.
- the compound is a five ring triterpene comprising at least two angeloyl group, attached to the side chains at one end of the five rings of its sapogenin and a sugar moiety is attached to the side chains of the ring at the other end of the triterpene.
- the compound comprising at least any two of angeloyl group, tigloyl group, or senecioyl group, or their combinations thereof.
- the compound is a sapogenin or triterpene comprising at least two angeloyl group, attached to the side chains of its sapogenin and a sugar moiety is attached to the side chains of the triterpene or sapogenin.
- the compound comprising at least any two of angeloyl group, tigloyl group, or senecioyl group, or their combinations thereof.
- the compound comprises at least two angeloyl group, attached to the side chains of a compound and a sugar moiety is attached to a side chain of the compound.
- the compound comprising at least any two of angeloyl group, tigloyl group, or senecioyl group, or their combinations thereof.
- the angeloyl can be replaced by a function group which has the function as angeloyl group.
- a sugar moiety or chain with one or more sugar such as D-glucose, D-galactose, L-rhamnose, L-arabinose, D-xylose, alduronic acid, D-glucuronic acid or D-galacturonic acid, or their combinations thereof, or their derivatives thereof is attached to carbon 3.
- the compound is a triterpene or sapongenin comprising at least any one of angeloyl group, tigloyl group or senecioyl group, or their combinations thereof attached to it.
- the compound is a triterpene or sapongenin comprising at least one of angeloyl group, tigloyl group or senecioyl group, or their combinations thereof attached to a sugar moiety which bonds to it.
- At least one sugar moiety with one or more sugar, D-glucose, D-galactose, L-rhamnose, L-arabinose, D-xylose, or alduronic acid, D-glucuronic acid or D-galacturonic acid, or their combinations thereof, or their derivatives thereof is attached to the triterpene.
- bonds 23-30 are attached with CH3 or CH2OH or COOH or acetyl group.
- the activities of a saponin compound for regulating or inhibiting tumor cell growth are based on or attributed to its structure that comprises functional group(s) such as angeloyl group, tigloyl group, senecioyl group or acetyl group, or their combinations thereof.
- the Compound Y1 and Compound Y2 which comprise with two angeloyl groups show the inhibition on the growth of ovarian cancer cells. See FIG. 29 .
- the Compound Y, Y8, Y9 and Y10 which comprise with two angeloyl groups show the inhibition on ovarian cancer cells as determined by MTT assay. See FIG. 30 .
- the compound with single angeloyl group shows weaker anticancer activity than a compound with two angeloyl groups. See FIG. 28 .
- the compound with two angeloyl groups is more potency than the one with on angeloyl for inhibiting human immunodeficiency virus (HIV), Severe Acute Respiratory Syndrome (SARS), flu disease or inhibits virus activities.
- HAV human immunodeficiency virus
- SARS Severe Acute Respiratory Syndrome
- flu disease flu disease or inhibits virus activities.
- composition comprising the compounds comprises the structure of:
- R1 and R2 are angeloyl group.
- R1 and R2 are angeloyl groups, tigloyl groups, senecioyl groups or acetyl group or their combinations.
- R1 and R2 comprise compound selected from angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, dibenzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, heterocylic or heteroraryl or derivative thereof.
- the above compounds can be used for inhibiting tumor cell growth, human immunodeficiency virus (HIV), Severe Acute Respiratory Syndrome (SARS) or flu disease, or capable of inhibiting viral activities, comprising contacting an effective amount of the above described compounds.
- HIV human immunodeficiency virus
- SARS Severe Acute Respiratory Syndrome
- flu disease or capable of inhibiting viral activities, comprising contacting an effective amount of the above described compounds.
- This invention provides a method of inhibiting the growth of ovarian cancer, breast cancer, brain cancer, bladder cancer, prostate cancer, bone cancer, skin cancer, leukocyte cancer, liver cancer or leukemia in a subject, comprising administering to a subject, in need thereof, an effective amount of the compound which comprises any of the above structures to said subject.
- This invention provides a method for inhibiting tumor cell growth, regulating cell growth, reducing inflammation, in a subject, comprising administering to a subject, in need thereof, an effective amount of the compound which comprises any of the above structures to said subject.
- This invention provides a method for reducing leg swelling, reducing the symptom of chronic venous insufficiency, peripheral edema, antilipemic, chronic venous disease, varicose vein disease, varicose syndrome, venous stasis, Expectorant, peripheral vascular disorders, cerebro-organic convulsion, cerebral circulation disorder, cerebral edema, psychoses, dysmenorrheal, hemorrhoids, episiotomies, haemonhoids, peripheral oedema formation or postoperative swelling; for reducing symptoms of leg pain; for treating pruritis, lower leg volume, for reducing symptoms of pain; thrombosis, thromophlebitis; for preventing gastric ulcers antispasmotic comprising administering to a subject, in need thereof, an effective amount of the composition of this invention.
- This invention provides a composition comprising the compounds of the invention for treating enuresis and frequency micturition, and for improving the functions of the central nervous system including signaling the bladder to wake up from deep sleep or to relax the bladder so that it can store more urine.
- the compounds of the invention can be used to relax the detrusor tension caused by aging, stress, nervousness, over-activity, instability, hyper-reflexia, and uninhibited bladder.
- the compounds may be used for relaxing the contracted bladder tissue induced by acetylcholine (Ach).
- the compounds identified and isolated from extract of this invention may be used as acetylcolinesterase, an AChE inhibitor, for regulating Antidiuretic hormone (ADH), which reduces the volume of urine, and as an anti-inflammatory agent.
- the compounds of the invention can be used for accelerating the growth of bladder, for suppressing deep sleep, for increasing alertness in a sleeping subject, for modulating the release, breakdown and uptake of Antidieuretic hormone (ADH) and its receptors, for modulating the secretion, breakdown and uptake of Adrenocorticotropic hormone (ACTH) and its receptors, for modulating the release, breakdown and uptake of 5-hydroxytryptamine and its receptors, for modulating the release, breakdown and uptake of Acetylcholine (Ach) and its receptors, for modulating the release, breakdown and uptake of Adrenaline (AD) and its receptors, for modulating the release, breakdown and uptake of Dopamine (DA) and its receptors, for modulating the release, breakdown and uptake of Norepinephrine (NE) and its receptors, for preventing sleep paralysis, for modulating the formation, release, breakdown and activity of neuropeptides and their receptors.
- ADH Antidieuretic hormone
- ACTH Adrenocorticotropic
- This invention provides a composition comprising the compounds of the invention for treating cancers; for inhibiting virus; for preventing cerebral aging; for improving memory; improving cerebral functions, for curing enuresis, frequent micturition, urinary incontinence, dementia, Alzheimer's disease, autism, brain trauma, Parkinson's disease or other diseases caused by cerebral dysfunctions; for treating arthritis, rheumatism, poor circulation, arteriosclerosis, Raynaud's syndrome, angina pectoris, cardiac disorder, coronary heart disease, headache, dizziness, kidney disorder; cerebrovascular disease; inhibiting NF-Kappa B activation; for treating brain edema, sever acute respiratory syndrome, respiratory viral diseases, chronic venous insufficiency, hypertension, chronic venous disease, anti-oedematous, anti inflammatory, haemonhoids, peripheral oedema formation, varicose vein disease, flu, post traumatic edema and postoperative swelling; for inhibiting ethanol absorption; for lowering blood sugar; for regulating the a
- This invention provides a composition for treating chronic venous insufficiency, peripheral edema, antilipemic, chronic venous disease, varicose vein disease, varicose syndrome, venous stasis, Expectorant, peripheral vascular disorders, cerebro-organic convulsion, cerebral circulation disorder, cerebral edema, psychoses, dysmenorrheal, hemorrhoids, episiotomies, haemonhoids, peripheral oedema formation or postoperative swelling; for reducing symptoms of pain; for reducing symptoms of stomach pain; for reducing symptoms of leg pain; for treating pruritis, lower leg volume, thrombosis, thromophlebitis; for preventing gastric ulcers antispasmotic.
- This invention provides a composition for AntiMS, antianeurysm, antiasthmatic, antibradykinic, anticapillarihemorrhagic, anticephalagic, anticervicobrachialgic, antieclamptic, antiedemic, antiencaphalitic, antiepiglottitic, antiexudative, antiflu, antifracture, antigingivitic, antihematomic, antiherpetic, antihistaminic, antihydrathritic, antimeningitic, antioxidant, antiperiodontic, antiphlebitic, antipleuritic, antiraucedo, antirhinitic, antitonsilitic, antiulcer, antivaricose, antivertiginous, cancerostatic, corticosterogenic, diuretic, fungicide, hemolytic, hyaluronidase inhibitor, lymphagogue, natriuretic, pesticide, pituitary stimulant, thymolytic, vasoprotective, venotonic treatment,
- an angeloyl group combined with a coumarin shows strong anti-tumor activities.
- This invention provides a compound capable of reducing or inhibiting cancer cell growth, comprising the following structure:
- Angeloyl or tigloyl or senecioyl or acetyl in the above compound is replaced with hydroxyl group, the anti-tumor activities will be lost.
- the replacement of Angeloyl group with tigloyl group also reduces the anti-tumor activities. If we replace the acetyl group with Angeloyl group, the anti-tumor activities is increased.
- Angeloyl group combined with a coumarin shows activities.
- the structure is shown below:
- the above described compounds can be used for inhibiting cancer, wherein the cancer is not limited to breast cancer, leukocyte cancer, liver cancer, ovarian cancer, bladder cancer, prostate cancer, bone cancer, skin cancer, lung cancer, brain cancer, cervix cancer, KB cancer or brain cancer.
- a sugar moiety is a segment of molecule comprising one or more sugar group.
- Alkenyl means, unsaturated linear or branched structures and combinations thereof, having 1-7 carbon atoms, one or more double bonds therein.
- alkenyl groups include vinyl, propenyl, isopropenyl, butenyl, s- and t-butenyl, pentenyl, hexenyl, butadienyl, pentadienyl, hexadienyl.
- An aryl is a functional group of organic molecule derived from an aromatic compound such as benzene, a 6-14 membered carbocyclic aromatic ring system comprising 1-3 benzene ring s. If two or more aromatic rings are present, then the rings are fused together, so that adjacent rings share a common bond. Examples include phenyl and naphthyl.
- the aryl group may be substituted with one or more substitutes independently selected from halogen, alkyl or alkoxy.
- Acyl is a function group obtained from an organic acid by the removal of the carboxyl.
- Acyl groups can be written as having the general formula —COR, where there is a double bond between the carbon and oxygen.
- the names of acyl groups typically end in -yl, such as formyl, acetyl, propionyl, butyryl, benzoyl.
- Benzoyl is one of acyls, C6H5.COR, obtained from benzoic acid by the removal of the carboxyl.
- heterocyclic compound a compound containing a heterocyclic ring which refers to a non-aromatic ring having 1-4 heteroatoms said ring being isolated or fused to a second ring selected from 3- to 7-membered alicyclic ring containing 0-4 heteroatoms, aryl and heteroaryl, wherein said heterocyclic include pyrrolidinyl, piperazinyl, morpholinyl, trahydrofuranyl, imidazolinyl thiomorpholinyl, and the like.
- heterocyclyl groups derived from heteroarenes by removal of a hydrogen atom from any ring atom
- alkanoyl is the general name for an organic functional group R.CO—, where R represents hydrogen nor an alkyl group.
- R represents hydrogen nor an alkyl group.
- alkanoyl is selected from acetyl, propionoyl, butyryl, isobutyryl, pentanoyl and hexanoyl.
- Alkenoyl is alkenylcarbonyl in which alkenyl is defined above. Examples are pentenoyl(tigloyl) and hexenoyl(angeloyl).
- Alkyl is a radical containing only carbon and hydrogen atoms arranged in a chain, branched, cyclic or bicyclic structure or their combinations, having 1-18 carbon atoms. Examples included but not limited to methyl, ethyl, propyl isopropyl, butyl, s- and t-butyl, pentyl, hexyl, heptyl, octyl, nonyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl.
- Absorption maximum Three absorption maximum were identified for plant extract; 207 nm, 278 nm and 500 nm.
- HTB-9 bladedder
- HeLa-S3 cervix
- DU145 prostate
- H460 lung
- MCF-7 breast
- K562 leukocytes
- HCT116 colon
- HepG2 liver
- U2OS bone
- T98G skin
- Skin OVCAR-3 (ovary).
- Cells were grown in culture medium (HeLa-S3, DU145, MCF-7, Hep-G2 and T98G in MEN (Earle's salts); HTB-9, H460, K562, OVCAR-3 in RPMI-1640; HCT-116, U2OS in McCoy-5A) supplemented with 10% fetal calf serum, glutamine and antibiotics in a 5% CO2 humidified incubator at 37° C.
- culture medium HeLa-S3, DU145, MCF-7, Hep-G2 and T98G in MEN (Earle's salts); HTB-9, H460, K562, OVCAR-3 in RPMI-1640; HCT-116, U2OS in McCoy-5A
- MTT assay The procedure for MTT assay followed the method described in (Carmichael et al., 1987) with only minor modifications.
- Cells were seeded into a 96-wells plate at concentrations of 10,000/well (HTB-9, HeLa, H460, HCT116, T98G, OVCAR-3), 15,000/well (DU145, MCF-7, HepG2, U2OS), or 40,000/well (K562), for 24 hours before drug-treatment. Cells were then exposed to drugs for 48 hours (72 hours for HepG2, U2OS, and 96 hours for MCF-7). After the drug-treatment, MTT (0.5 mg/ml) was added to cultures for an hour.
- the response of the cell lines to the tested extract can be categorized into four groups: Most sensitive, Sensitive; Semi-sensitive; and least sensitive.
- the plant extract was fractionated.
- Sample loading 1-2 ml, concentration: 100 mg/ml in 10% acetonitrile/TFA.
- Fraction Collector 5 ml/fractions (collect from 10% to 72% acetonitrile)
- Instrument AKTA-FPLC, P920 pump; Monitor UPC-900; Frac-900.
- NMR analysis The pure compound Y of Xanthoceras sorbifolia was dissolved in pyridine-D5 with 0.05% v/v TMS. All NMR spectra were acquired using a Bruker Avance 600 MHz NMR spectrometer with a QXI probe (1H/13C/15N/31P) at 298 K. The numbers of scans for 1D 1H spectra were 16 to 128, depending on the sample concentration. 2D HMQC spectra were recorded with spectral widths of 6000 ⁇ 24,000 Hz and data points of 2024 ⁇ 256 for t2 and t1 dimensions, respectively. The number of scans was 4 to 128.
- 2D HMBC were acquired with spectral widths of 6000 ⁇ 30,000 Hz and data points of 2024 ⁇ 512 for t2 and t 1 dimensions, respectively.
- the number of scans was 64.
- the 2D data were zero-filled in t 1 dimension to double the data points, multiplied by cosine-square-bell window functions in both t 1 and t 2 dimensions, and Fourier-transformed using software XWIN-NMR.
- the final real matrix sizes of these 2D spectra are 2048 ⁇ 256 and 2048 ⁇ 512 data points (F2 ⁇ F1) for HMQC and HMBC, respectively.
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Abstract
Description
- R5=Bor C or S1 (see note 1)
- R1=A or B or C
- R2=A or B or C
- R4=A or B or C
- A=angeloyl or Tigloyl or Senecioyl
- B=acetyl
- C=H
- S1=sugar moiety comprising one or more sugar, D-glucose, D-galactose, L-rhamnose, L-arabinose, D-xylose, alduronic acid, D-glucuronic acid, D-galacturonic acid, or their derivatives.
- R5=B or C or S1 (see note 1)
- R1=A or B or C
- R2=A or B or C
- R3=A or B or C
- R4=A or B or C
- A=angeloyl or Tigloyl or Senecioyl
- B=acetyl
- C=H
- S1=sugar moiety comprising one or more sugar, D-glucose, D-galactose, L-rhamnose, L-arabinose, D-xylose, alduronic acid, D-glucuronic acid, D-galacturonic acid, or their derivatives.
- R5=B or C or S1 (see note 1)
- R1=A or B or C
- R2=A or B or C
- R3=A or B or C
- R4=A or B or C
- A=angeloyl or Tigloyl or Senecioyl
- B=acetyl
- C=H
- S1=sugar moiety comprising one or more sugar, D-glucose, D-galactose, L-rhamnose, L-arabinose, D-xylose, alduronic acid, D-glucuronic acid, D-galacturonic acid, or their derivatives.
- Wherein R1=angeloyl group or tigloyl group or senecioyl group or H.
- R2=angeloyl group or tigloyl group or senecioyl group or acetyl group or H.
- R3=angeloyl group or tigloyl group or senecioyl group or acetyl group or H.
- Wherein R1=angeloyl group or tigloyl group or senecioyl group or H.
- R2=angeloyl group or tigloyl group or senecioyl group or acetyl group or H.
- R3=angeloyl group or tigloyl group or senecioyl group or acetyl group or H.
- R6=H or OH
- Wherein R1=angeloyl group or tigloyl group or senecioyl group or H.
- R2=angeloyl group or tigloyl group or senecioyl group or acetyl group or H.
- R3=angeloyl group or tigloyl group or senecioyl group or acetyl group or H.
- R4=OH or H
- Wherein R1=angeloyl group or tigloyl group or senecioyl group or acetyl group or H.
- R2=angeloyl group or tigloyl group or senecioyl group or acetyl group or H.
- R3=Acetyl or H.
- R8=H or OH
- Wherein R1=angeloyl group or tigloyl group or senecioyl group or acetyl group or H.
- R2=angeloyl group or tigloyl group or senecioyl group or acetyl group or H.
- R3=Acetyl or H.
- R4=CH3 or CH2OH or COOH
- R6=CH3 or CH2OH or COOH
- R8=H or OH
- Wherein R1=angeloyl group or tigloyl group or senecioyl group or acetyl group or H.
- R2=angeloyl group or tigloyl group or senecioyl group or acetyl group or H.
- R3=Acetyl or H.
- R4=COOH OR COOMe or CH2OH
- R5=α-L-araf and R6=α-L-arap and R7=β-D-glup; or R5, R6, and R7 is a sugar moiety, or D-glucose, or D-galactose, or L-rhamnose, or L-arabinose, or D-xylose, or alduronic acid, or D-glucuronic acid, or D-galacturonic acid, or their derivatives.
- Wherein R1=angeloyl group or tigloyl group or senecioyl group or acetyl group or H.
- R2=angeloyl group or tigloyl group or senecioyl group or acetyl group or H.
- R3=CH2OH or CH3 or CHO
- Wherein R1=angeloyl group or tigloyl group or senecioyl group or acetyl group or H.
- R2=angeloyl group or tigloyl group or senecioyl group or acetyl group or H.
- R3=CH2OH or CH3 or CHO
- Wherein R1=angeloyl group or tigloyl group or senecioyl group or acetyl group or H.
- R2=angeloyl group or tigloyl group or senecioyl group or acetyl group or H.
- R3=CH2OH or CH3 or CHO or COOCH3
- R4=S1=sugar moiety comprising one or more sugar, D-glucose, D-galactose, L-rhamnose, L-arabinose, D-xylose, alduronic-acid, D-glucuronic acid, D-galacturonic acid, or/and their derivatives.
- Wherein R1=angeloyl group or tigloyl group or senecioyl group or acetyl group or H.
- R2=angeloyl group or tigloyl group or senecioyl group or acetyl group or H.
- R3=CH2OH or CH3 or CHO or COOCH3
- R4=sugar moiety comprising one or more sugar, D-glucose, D-galactose, L-rhamnose, L-arabinose, D-xylose, alduronic acid, D-glucuronic acid, D-galacturonic acid, or/and their derivatives.
- Wherein R2=angeloyl group or tigloyl group or senecioyl group or acetyl group or H.
- R3=angeloyl group or tigloyl group or senecioyl group or acetyl group or H.
- R4=CH2OH or CH3 or CHO or COOCH3
- R1=sugar moiety comprising one or more sugar, D-glucose, D-galactose, L-rhamnose, L-arabinose, D-xylose, alduronic acid, D-glucuronic acid, D-galacturonic acid, or/and their derivatives.
- Wherein R1=angeloyl group or tigloyl group or senecioyl group or propanoyl or butanoly or acetyl group or H.
- R2=angeloyl group or tigloyl group or senecioyl group or propanoyl or butanoly or acetyl group or H.
- R3=angeloyl group or tigloyl group or senecioyl group or propanoyl or butanoly or acetyl group or H.
- R4=sugar moiety comprising one or more sugar, D-glucose, D-galactose, L-rhamnose, L-arabinose, D-xylose, alduronic acid, D-glucuronic acid, D-galacturonic acid, or/and their derivatives.
- R1=angeloyl or Tigloyl or Senecioyl or acetyl or H
- R2=angeloyl or Tigloyl or Senecioyl or acetyl or H
- R6=angeloyl or Tigloyl or Senecioyl or acetyl or H
- R3=H or OH
- R10=CH3 or CH2OH or CHO
- R5=D-glucose or D-galactose or L-rhamnose or L-arabinose or, D-xylose or alduronic acid or D-glucuronic acid or D-galacturonic acid or H
- R7=D-glucose or D-galactose or L-rhamnose or L-arabinose or, D-xylose or alduronic acid or D-glucuronic acid or D-galacturonic acid or H
- R8=D-glucose or D-galactose or L-rhamnose or L-arabinose or, D-xylose or alduronic acid or D-glucuronic acid or D-galacturonic acid or H
- R9=COOH or CH2OH
- R1=angeloyl or tigloyl or senecioly or acetyl group or H
- R2=angeloyl or tigloyl or senecioly or acetyl group or H
- R3=angeloyl or tigloyl or senecioly or acetyl group or H
- R6=H
- R4=CH3 or CH2OH or COOH
- R1=angeloyl or tigloyl or senecioly or acetyl group or H
- R2=angeloyl or tigloyl or senecioly or acetyl group or H
- R3=angeloyl or tigloyl or senecioly or acetyl group or H
- R6=angeloyl or tigloyl or senecioly or acetyl group or H
- R4=CH3 or CH2OH or COOH
- R5=acetyl or H or S1 (see note 1)
- R1=angeloyl or tigloyl or senecioly or acetyl group or H
- R2=angeloyl or tigloyl or senecioly or acetyl group or H
- R3=angeloyl or tigloyl or senecioly or acetyl group or H
- R6=angeloyl or tigloyl or senecioly or acetyl group or H
- R4=CH3 or CH2OH or COOH
- R5=acetyl or H or S1 (see note 1)
- S1=sugar moiety comprises one or more sugar, D-glucose, D-galactose, L-rhamnose, L-arabinose, D-xylose, alduronic acid, D-glucuronic acid, D-galacturonic acid, or/and their derivatives.
- R2, R3, R5, R6, R8, R9=angeloyl or tigloyl or senecioly or acetyl or H
- R4=CH3 or CH2OH or COOH
- S1=Sugar moiety comprises one or more sugar, D-glucose, D-galactose, L-rhamnose, L-arabinose, D-xylose, alduronic acid, D-glucuronic acid, D-galacturonic acid, or/and their derivatives.
- R2, R3, R5, R6, R8, R9=angeloyl or tigloyl or senecioly or acetyl or H
- R4, R7=CH3 or CH2OH or COOH
- (a) extracting roots, kernel, leave, bark, stem, husk, seed, seed shell or fruit or combinations thereof of the above plant with organic solvents such as ethanol or methanol to obtain a organic extract;
- (b) collecting the organic extract;
- (c) refluxing the organic extract to obtain a second extract;
- (d) removing the organic solvent from the second extract to obtain a third extract;
- (e) drying and sterilizing the third extract to obtain a crude extract powder;
- (f) fractionating the crude extract powder into fractions or components. Fractionation may be achieved by HPLC and FPLC chromatography with silica gel, C18 or other equivalent solid phase materials;
- (g) monitoring the fractions. If using HPLC or FPLC, absorption wavelength at 207 nm to 500 nm may be used;
- (h) identifying the bioactive components of the crude extract;
- (i) purifying one or more bioactive components of the crude extract with chromatographic techniques that employ FPLC to obtain one or more fraction of the bioactive component; and
- (j) isolating the bioactive components with chromatographic techniques that employ preparative columns and HPLC.
% G=(TD−T0/TC−T0)×100 (1),
where TC or TD represent O.D. readings of control or drug-treated cells. When T0>TD, then the cytotoxicity (LC) expressed as % of the control is calculated as:
% LC=(TD−T0/T0)×100 (2)
or a salt, ester, metabolite or derivative thereof, wherein R1 and R2 represent angeloyl group; R3 represents H or OH; R4 represent CH2OR6; and wherein R6 is H; R5 represents at least one sugar moiety or its derivatives.
or a salt, ester or derivative thereof, wherein R1 represents angeloyl group; R2 represents angeloyl group; R3 represents OH or H; Positions 23, 24, 25, 26, 27, 29, of the compound independently comprise CH3, or CH2OH, or CHO, or COOH, alkyls group, or acetyl group, or derivative; R6 represents Ac or H; and R5 represents sugar moiety, wherein the sugar moiety comprises at least one sugar, or D-glucose, or D-galactose, or L-rhamnose, or L-arabinose, or D-xylose, or alduronic acid, or D-glucuronic acid, or D-galacturonic acid, or their derivative thereof, or the combination thereof. In an embodiment, R5 represents a compound capable of performing the function of the sugar moiety. In another embodiment the sugar moiety comprises L-arabinose, D-glucose and/or D-galactose, or combinations thereof. In a further embodiment, any two of R1, R2 or R6 are angeloyl groups, or any one of R1, R2 or R6 is attached to a sugar moiety in which two angeloyl groups are attached to adjacent carbons of the monosaccharides. In a further embodiment, R1, R2, and R6 comprises angeloyl group, acetyl group, tigloyl group, senecioly group, or an acid with two to five carbons or combination thereof. In a further embodiment, at least one of R1, R2 or R6 is attached a sugar moiety, wherein sugar moiety comprises two angeloyl group, acetyl group, tigloyl group, senecioly group, acid having two to five carbons, or combinations thereof.
or a salt, ester or derivative thereof, wherein R1 represents angeloyl group; R2 represents angeloyl group; R3 represents OH or H; R4 represents CH3 or CH2OH or alkyls group or their derivatives; R6 represents Ac or H and R5 represents sugar moiety, wherein the sugar moiety comprises at least one sugar, or D-glucose, or D-galactose, or L-rhamnose, or L-arabinose, or D-xylose, or alduronic acid, or D-glucuronic acid, or D-galacturonic acid, or derivative thereof, or the combination thereof. In an embodiment, R5 represents a compound capable of performing the function of sugar moiety. In another embodiment the sugar moiety comprises L-arabinose, or D-glucose, or D-galactose, or combinations thereof. In a further embodiment, at least one of R1, R2 or R6 is attached a sugar moiety or rhamnose, wherein sugar moiety or rhamnose comprises two angeloyl group, acetyl group, tigloyl group, senecioly group, acid having two to five carbons, or combinations thereof.
or a salt, ester, metabolite or derivative thereof, wherein R1 and R2 represent angeloyl group; R3 represents H or OH; R4 represent CH2OR6; and wherein R6 is H or acetyl; R5 represents sugar moiety or D-glucose; R7 represents a sugar moiety or L-arabinose; R8 represents sugar moiety or D-galactose; R9 represent COOH or CH2OH.
or a salt, ester, metabolite or derivative thereof, wherein R1 and R2 represent angeloyl group; R3 represents H or OH; R6 represent H or acetyl; R9 represents COOH or CH2OH; R10 represent CH3 or CH2OH or COOH; R5, R7 and R8 are H or/and sugar moiety, wherein the sugar moiety comprises at least one sugar, D-glucose, D-galactose, L-rhamnose, L-arabinose, D-xylose, alduronic acid, D-glucuronic acid, or D-galacturonic acid, or derivative thereof. In an embodiment, at least one of R1, R2, and R6 is a sugar moiety or compound comprising at least two angeloyl groups, acetyl group, tigloyl group, senecioly group, or an acid having two to five carbons or combination thereof. In another embodiment, at least two of R1, R2, and R6 comprise an angeloyl group
or a salt, ester or derivative thereof, wherein R1 represents angeloyl group; R2 represents angeloyl group; R3 represents OH or H; R4 represents CH3 or CH2OH; R7 represents H; and R5 represents D-glucose, D-Galactose, L-arabinose or H; and R6 represents D-glucose, D-Galactose, L-arabinose or H. In an embodiment, R5 or/and R6 are H or sugar moiety comprises at least one sugar, D-glucose, D-galactose, L-rhamnose, L-arabinose, D-xylose, alduronic acid, D-glucuronic acid, or D-galacturonic acid, or derivative thereof.
or a salt, ester, metabolite or derivative thereof, wherein R1 and R2 independently represent angeloyl group; R3 represents H or OH; R4 represent CH2OR6; and wherein R6 is H; R5 represents at least one sugar moiety or its derivatives.
or a salt, ester, metabolite or derivative thereof, wherein R1 comprise compound selected from hydrogen, angeloyl, acetyl, tigloyl, senecioyl, alkyl, dibenzoyl, benzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, heterocylic or heteroraryl or derivative thereof; R2 comprise compound selected from hydrogen, angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, dibenzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl or derivative thereof; R4 represents CH2OR6, COOR6 wherein R6 is selected from hydrogen, angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, dibenzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl or derivative thereof; R3 is H or OH; R5 represents sugar moiety, wherein the sugar moiety comprises at least one sugar, D-glucose, D-galactose, L-rhamnose, L-arabinose, D-xylose, alduronic acid, D-glucuronic acid or D-galacturonic acid or derivative thereof, or the combination thereof.
or a salt, ester, metabolite or derivative thereof, wherein R1 and R2 independently represent angeloyl group; R3 represents H or OH; R4 represent CH2OR6 wherein R6 is H; R5 represents sugar moiety or D-glucose, D-galactose or its derivatives. R7 represent COOH
or a salt, ester, metabolite or derivative thereof, wherein R1 comprise compound selected from hydrogen, angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl or derivative thereof; R2 comprise compound selected from hydrogen, angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl or derivative thereof; R4 represents CH2OR6, COOR6 wherein R6 is selected from hydrogen, angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, acyl, heterocylic or heteroraryl or derivative thereof; R3 is H or OH; R5 represents sugar moiety, or D-glucose or D-galactose; R7 represent COOH
- 3-O-{[β-D-galactopyranosyl(1→2)]-[α-L-arabinofuranosyl(1→3)]-β-D-glucuronopyranoside butyl ester}-21-O-acetyl-22-O-angeloyl-3β, 16α, 21β, 22α, 28-pentahydroxyolean-12-ene.
- 3-O-[β-D-galactopyranosyl(1→2)]-α-L-arabinofuranosyl(1→3)-β-D-glucuronopyranosyl-21,22-O-diangeloyl-3β, 15α, 16α, 21β, 22α, 28-hexahydroxyolean-12-ene,
- 3-O-[β-D-galactopyranosyl(1→2)]-α-L-arabinofuranosyl(1→3)-β-D-glucuronopyranosyl-21-O-(3,4-diangeloyl)-α-L-rhamnophyranosyl-22-O-acetyl-3β, 16α, 21β, 22α, 28-pentahydroxyolean-12-ene,
- 3-O-[β-D-glucopyranosyl-(1→2)]-α-L-arabinofuranosyl(1→3)-β-D-glucuronopyranosyl-21,22-O-diangeloyl-3β, 15α, 16α, 21β, 22α, 24β, 28-heptahydroxyolean-12-ene,
- 3-O-[β-glucopyranosyl(1→2)]-α-arabinofuranosyl(1→3)-β-glucuronopyranosyl-21,22-O-diangeloyl-3β, 16α, 21β, 22α, 24β, 28-hexahydroxyolean-12-ene,
- 3-O-[β-galactopyranosyl(1→2)]-α-arabinofuranosyl(1→3)-β-glucuronopyranosyl-21-O-(3,4-diangeloyl)-α-rhamnopyranosyl-28-O-acetyl-3β, 16α, 21β, 22α, 28-pentahydroxyolean-12-ene,
- 3-O-[β-galactopyranosyl(1→2)]-α-arabinofuranosyl(1→3)-β-glucuronopyranosyl-21,22-O-diangeloyl-3β, 16α, 21β, 22α, 28-pentahydroxyolean-12-ene,
- A) 3-O-[β-D-galactopyranosyl(1→2)]-α-L-arabinofuranosyl(1→3)-β-D-glucuronopyranosyl-21,22-O-diangeloyl-3β, 15α, 16α, 21β, 22α, 28-hexahydroxyolean-12-ene,
- B) 3-O-[β-D-galactopyranosyl(1→2)]-α-L-arabinofuranosyl(1→3)-β-D-glucuronopyranosyl-21-O-(3,4-diangeloyl)-α-L-rhamnophyranosyl-22-O-acetyl-3β, 16α, 21β, 22α, 28-pentahydroxyolean-12-ene
- C) 3-O-[β-D-glucopyranosyl-(1→2)]-α-L-arabinofuranosyl(1→3)-(-D-glucuronopyranosyl-21,22-O-diangeloyl-3β, 15α, 16α, 21β, 22α, 24β, 28-heptahydroxyolean-12-ene
- D) 3-O-[β-galactopyranosyl(1→2)]-α-arabinofuranosyl(1→3)-β-glucuronopyranosyl-21,22-O-diangeloyl-3β, 16α, 21β, 22α, 28-pentahydroxyolean-12-ene
- E) 3-O-[β-galactopyranosyl(1→2)]-α-arabinofuranosyl(1→3)-β-glucuronopyranosyl-21-O-(3,4-diangeloyl)-α-rhamnopyranosyl-28-O-acetyl-3β, 16α,21β, 22α, 28-pentahydroxyolean-12-ene
- F) 3-O-[β-galactopyranosyl(1→2)]-α-arabinofuranosyl(1→3)-β-glucuronopyranosyl-21,22-O-diangeloyl-3β, 16α, 21β, 22α, 28-pentahydroxyolean-12-ene
- G) 3-O-[β-D-galactopyranosyl(1→2)]-α-L-arabinofuranosyl(1→3)-β-D-glucuronopyranosyl-21,22-O-dibenzoyl-3β, 15α, 16α, 21β, 22α, 28-hexahydroxyolean-12-ene,
- H) 3-O-[β-D-galactopyranosyl(1→2)]-α-L-arabinofuranosyl(1→3)-β-D-glucuronopyranosyl-21-O-(3,4-dibenzoyl)-α-L-rhamnophyranosyl-22-O-acetyl-3β, 16α, 21β, 22α, 28-pentahydroxyolean-12-ene
- I) 3-O-[β-D-glucopyranosyl-(1→2)]-α-L-arabinofuranosyl(1→3)-(-D-glucuronopyranosyl-21,22-O-dibenzoyl-3β, 15α, 16α, 21β, 22α, 24β, 28-heptahydroxyolean-12-ene
- J) 3-O-[β-galactopyranosyl(1→2)]-α-arabinofuranosyl(1→3)-β-glucuronopyranosyl-21,22-O-dibenzoyl-3β, 16α, 21β, 22α, 28-pentahydroxyolean-12-ene
- K) 3-O-[β-galactopyranosyl(1→2)]-α-arabinofuranosyl(1→3)-β-glucuronopyranosyl-21-O-(3,4-dibenzoyl)-α-rhamnopyranosyl-28-O-acetyl-3β, 16α, 21β, 22α, 28-pentahydroxyolean-12-ene
- L) 3-O-[β-galactopyranosyl(1→2)]-α-arabinofuranosyl(1→3)-β-glucuronopyranosyl-21,22-O-dibenzoyl-3β, 16α, 21β, 22α, 28-pentahydroxyolean-12-ene
- M) 3-O-[β-D-galactopyranosyl(1→2)]-β-D-xyopyranosyl(1→3)-β-D-glucuronopyranosyl-21,22-O-dibenzoyl-3β, 15α, 16α, 21β, 22α, 28-hexahydroxyolean-12-ene,
- N) 3-O-[β-D-galactopyranosyl(1→2)]-β-D-xyopyranosyl(1→3)-β-D-glucuronopyranosyl-21-O-(3,4-dibenzoyl)-α-L-rhamnophyranosyl-22-O-acetyl-3β, 16α, 21β, 22α, 28-pentahydroxyolean-12-ene
- O) 3-O-[β-D-glucopyranosyl-(1→2)]-β-D-xyopyranosyl(1→3)-(-D-glucuronopyranosyl-21,22-O-dibenzoyl-3β, 15α, 16α, 21β, 22α, 24β, 28-heptahydroxyolean-12-ene
- P) 3-O-[β-D-galactopyranosyl(1→2)]-β-D-xyopyranosyl(1→3)-β-D-glucuronopyranosyl-21,22-O-dibenzoyl-3β, 16α, 21β, 22α, 28-pentahydroxyolean-12-ene
- Q) 3-O-[β-galactopyranosyl(1→2)]-β-xyopyranosyl(1→3)-β-glucuronopyranosyl-21-O-(3,4-dibenzoyl)-α-rhamnopyranosyl-28-O-acetyl-3β, 16α, 21β, 22α, 28-pentahydroxyolean-12-ene
- R) 3-O-[β-galactopyranosyl(1→2)]-β-xyopyranosyl(1→3)-β-glucuronopyranosyl-21,22-O-dibenzoyl-3β, 16α, 21β, 22α, 28-pentahydroxyolean-12-ene
- S) 3-O-[β-D-galactopyranosyl(1→2)]-β-D-xyopyranosyl(1→3)-β-D-glucuronopyranosyl-21,22-O-diangeloyl-3β, 15α, 16α, 21β, 22α, 28-hexahydroxyolean-12-ene,
- T) 3-O-[β-D-galactopyranosyl(1→2)]-β-D-xyopyranosyl(1→3)-β-D-glucuronopyranosyl-21-O-(3,4-diangeloyl)-α-L-rhamnophyranosyl-22-O-acetyl-3β, 16α, 21β, 22α, 28-pentahydroxyolean-12-ene
- U) 3-O-[β-D-glucopyranosyl-(1→2)]-β-D-xyopyranosyl(1→3)-(-D-glucuronopyranosyl-21,22-O-diangeloyl-3β, 15α, 16α, 21β, 22α, 24β, 28-heptahydroxyolean-12-ene
- V) 3-O-[β-galactopyranosyl(1→2)]-β-D-xyopyranosyl(1→3)-β-glucuronopyranosyl-21,22-O-diangeloyl-3β, 16α, 21β, 22α, 28-pentahydroxyolean-12-ene
- W) 3-O-[β-galactopyranosyl(1→2)]-β-D-xyopyranosyl(1→3)-β-glucuronopyranosyl-21-O-(3,4-diangeloyl)-α-rhamnopyranosyl-28-O-acetyl-3β, 16α, 21β, 22α, 28-pentahydroxyolean-12-ene
- X) 3-O-[β-D-galactopyranosyl(1→2)]-β-D-xyopyranosyl(1→3)-β-D-glucuronopyranosyl-21,22-O-diangeloyl-3β, 16α, 21β, 22α, 28-pentahydroxyolean-12-ene
- A) 3-O-[β-D-galactopyranosyl(1→2)]-α-L-arabinofuranosyl(1→3)-β-D-glucuronopyranosyl-21-O-angeloyl,22-O-benzoyl-3β, 15α, 16α, 21β, 22α, 28-hexahydroxyolean-12-ene,
- B) 3-O-[β-D-galactopyranosyl(1→2)]-α-L-arabinofuranosyl(1→3)-β-D-glucuronopyranosyl-21-O-(3-angeloyl,4-benzoyl)-α-L-rhamnophyranosyl-22-O-acetyl-3β, 16α, 21β, 22α, 28-pentahydroxyolean-12-ene
- C) 3-O-[β-D-glucopyranosyl-(1→2)]-α-L-arabinofuranosyl(1→3)-(-D-glucuronopyranosyl-21-O-angeloyl,22-O-benzoyl-3β, 15α, 16α, 21β, 22α, 24β, 28-heptahydroxyolean-12-ene
- D) 3-O-[β-galactopyranosyl(1→2)]-α-arabinofuranosyl(1→3)-β-glucuronopyranosyl-21-O-angeloyl,22-benzoyl-3β, 16α, 21β, 22α, 28-pentahydroxyolean-12-ene
- E) 3-O-[β-galactopyranosyl(1→2)]-α-arabinofuranosyl(1→3)-β-glucuronopyranosyl-21-O—F) (3-angeloyl,4-benzoyl)-α-rhamnopyranosyl-28-O-acetyl-3β, 16α, 21β, 22α, 28-pentahydroxyolean-12-ene
- F) 3-O-[β-galactopyranosyl(1→2)]-α-arabinofuranosyl(1→3)-β-glucuronopyranosyl-21-O-angeloyl,22-O-benzoyl-3β, 16α, 21β, 22α, 28-pentahydroxyolean-12-ene
- G) 3-O-[β-D-galactopyranosyl(1→2)]-α-L-arabinofuranosyl(1→3)-β-D-glucuronopyranosyl-21-O-benzoyl,22-O-angeloyl-3β, 15α, 16α, 21β, 22α, 28-hexahydroxyolean-12-ene,
- H) 3-O-[β-D-galactopyranosyl(1→2)]-α-L-arabinofuranosyl(1→3)-β-D-glucuronopyranosyl-21-O-(3-benzoyl,4-angeloyl)-α-L-rhamnophyranosyl-22-O-acetyl-3β, 16α, 21β, 22α, 28-pentahydroxyolean-12-ene
- I) 3-O-[β-D-glucopyranosyl-(1→2)]-α-L-arabinofuranosyl(1→3)-(-D-glucuronopyranosyl-21-O-benzoyl,22-O-angeloyl-3β, 15α, 16α, 21β, 22α, 24β, 28-heptahydroxyolean-12-ene
- J) 3-O-[β-galactopyranosyl(1→2)]-α-arabinofuranosyl(1→3)-β-glucuronopyranosyl-21-O-benzoyl,22-O-angeloyl-3β, 16α, 21β, 22α, 28-pentahydroxyolean-12-ene
- K) 3-O-[β-galactopyranosyl(1→2)]-α-arabinofuranosyl(1→3)-β-glucuronopyranosyl-21-O-(3-benzoyl,4-angeloyl)-α-rhamnopyranosyl-28-O-acetyl-3β, 16α, 21β, 22α, 28-pentahydroxyolean-12-ene
- L) 3-O-[β-galactopyranosyl(1→2)]-α-arabinofuranosyl(1→3)-β-glucuronopyranosyl-21-O-benzoyl,22-O-angeloyl-3β, 16α, 21β, 22α, 28-pentahydroxyolean-12-ene
- M) 3-O-[β-D-galactopyranosyl(1→2)]-β-D-xyopyranosyl(1→3)-β-D-glucuronopyranosyl-21-O-angeloyl,22-O-benzoyl-3β, 15α, 16α, 21β, 22α, 28-hexahydroxyolean-12-ene,
- N) 3-O-[β-D-galactopyranosyl(1→2)]-β-D-xyopyranosyl(1→3)-β-D-glucuronopyranosyl-21-O-(3-angeloyl,4-dibenzoyl)-α-L-rhamnophyranosyl-22-O-acetyl-3β, 16α, 21β, 22α, 28-pentahydroxyolean-12-ene
- O) 3-O-[β-D-glucopyranosyl-(1→2)]-β-D-xyopyranosyl(1→3)-(-D-glucuronopyranosyl-21-O-21-O-angeloyl,22-O-benzoyl-3β, 15α, 16α, 21β, 22α, 24β, 28-heptahydroxyolean-12-ene
- P) 3-O-[β-D-galactopyranosyl(1→2)]-β-D-xyopyranosyl(1→3)-β-D-glucuronopyranosyl-2121-O-angeloyl,22-O-benzoyl-3β, 16α, 21β, 22α, 28-pentahydroxyolean-12-ene
- Q) 3-O-[β-galactopyranosyl(1→2)]-β-xyopyranosyl(1→3)-β-glucuronopyranosyl-21-O-(3-angeloyl,4-dibenzoyl)-α-rhamnopyranosyl-28-O-acetyl-3β, 16α, 21β, 22α, 28-pentahydroxyolean-12-ene
- R) 3-O-[β-galactopyranosyl(1→2)]-β-xyopyranosyl(1→3)-β-glucuronopyranosyl-angeloyl,22-O-benzoyl-3β, 16α, 21β, 22α, 28-pentahydroxyolean-12-ene
- S) 3-O-[β-D-galactopyranosyl(1→2)]-β-D-xyopyranosyl(1→3)-β-D-glucuronopyranosyl-21-O-benzoyl,22-O-angeloyl-3β, 15α, 16α, 21β, 22α, 28-hexahydroxyolean-12-ene,
- T) 3-O-[β-D-galactopyranosyl(1→2)]-β-D-xyopyranosyl(1→3)-β-D-glucuronopyranosyl-21-O-(3-benzoyl,4-angeloyl)-α-L-rhamnophyranosyl-22-O-acetyl-3β, 16α, 21β, 22α, 28-pentahydroxyolean-12-ene
- U) 3-O-[β-D-glucopyranosyl-(1→2)]-β-D-xyopyranosyl(1→3)-(-D-glucuronopyranosyl-21-O-benzoyl,22-O-angeloyl-3β, 15α, 16α, 21β, 22α, 24β, 28-heptahydroxyolean-12-ene
- V) 3-O-[β-galactopyranosyl(1→2)]-β-D-xyopyranosyl(1→3)-β-glucuronopyranosyl-21-O-benzoyl,22-O-angeloyl-3β, 16α, 21β, 22α, 28-pentahydroxyolean-12-ene
- W) 3-O-[β-galactopyranosyl(1→2)]-β-D-xyopyranosyl(1→3)-β-glucuronopyranosyl-21-O-(3-benzoyl,4-angeloyl)-α-rhamnopyranosyl-28-O-acetyl-3β, 16α, 21β, 22α, 28-pentahydroxyolean-12-ene
- X) 3-O-[D-galactopyranosyl(1→2)]-β-D-xyopyranosyl(1→3)-β-D-glucuronopyranosyl-21-O-benzoyl,22-O-angeloyl-3β, 16α, 21β, 22α, 28-pentahydroxyolean-12-ene
Wherein | | R2 | R3 | |
1 | | Acetyl | H | |
2 | | Acetyl | H | |
3 | | H | H | |
4 | Angeloyl | H | Acetyl | |
5 | H | Tigloyl | Acetyl | |
6 | H | Angeloyl | Acetyl | |
7 | H | H | Tigloyl | |
8 | H | H | Angeloyl | |
- Wherein R1=angeloyl group or tigloyl group or senecioyl group or acetyl or H.
- R2=angeloyl group or tigloyl group or senecioyl group or acetyl group or acetyl or H.
- R3=angeloyl group or tigloyl group or senecioyl group or acetyl group or acetyl or H.
- R6=H or OH
- Wherein R1=angeloyl or Tigloyl or Senecioyl or acetyl or H
- R2=angeloyl or Tigloyl or Senecioyl or acetyl or H
- R6=angeloyl or Tigloyl or Senecioyl or acetyl or H
- R3=H or OH
- R10=CH3 or CH2OH or CHO
- R5=sugar moiety or D-glucose or D-galactose or L-rhamnose or L-arabinose or, D-xylose or alduronic acid or D-glucuronic acid or D-galacturonic acid or H
- R7=sugar moiety or D-glucose or D-galactose or L-rhamnose or L-arabinose or, D-xylose or alduronic acid or D-glucuronic acid or D-galacturonic acid or H
- R8=sugar moiety or D-glucose or D-galactose or L-rhamnose or L-arabinose or, D-xylose or alduronic acid or D-glucuronic acid or D-galacturonic acid or H
- R9=COOH or CH2OH
- Wherein R1=angeloyl group.
- R2=senecioyl group.
R1 | | R3 | R4 | ||
1. | 2-acetoxy-2- | acetyl | | COOH | ||
methybutanoyl | ||||||
2. | Angeloyl | | H | COOH | ||
3. | Angeloyl | | acetyl | COOH | ||
4. | Angeloyl | | H | COOH | ||
5. | H | | H | COOH | ||
7. | H | | H | COOMe | ||
8. | H | H | H | CH2OH | ||
R5 = α-L-araf | ||||||
R6 = α-L-arap | ||||||
R7 = β-D-glup |
compound | | R2 | R3 | |
2 | acetyl | H | angeloyl |
3 | H | acetyl | angeloyl |
5 | H | propanoyl | angeloyl |
7 | H | butanoyl | angeloyl |
8 | H | angeloyl | angeloyl |
4 | acetyl | acetyl | angeloyl |
6 | acetyl | propanoyl | angeloyl |
9 | acetyl | butanoyl | angeloyl |
10 | acetyl | angeloyl | angeloyl |
wherein R1 and R2 are angeloyl group. In embodiment, R1 and R2 are angeloyl groups, tigloyl groups, senecioyl groups or acetyl group or their combinations. In embodiment, R1 and R2 comprise compound selected from angeloyl, acetyl, tigloyl, senecioyl, alkyl, benzoyl, dibenzoyl, alkanoyl, alkenoyl, benzoyl alkyl substituted alkanoyl, aryl, heterocylic or heteroraryl or derivative thereof.
- Wherein the R1, R2=Angeloyl, or tigloyl, or senecioyl, or acetyl group.
- Wherein the R1, R2=Angeloyl or tigloyl or senecioyl or acetyl group.
- Wherein the R1, R2=Angeloyl or tigloyl or senecioyl or actyl group.
% G=(TD−T0/TC−T0)×100 (1)
where TC or TD represent O.D. readings of control or drug-treated cells. When T0>TD, then the cytotoxicity (LC) expressed as % of the control is calculated as:
% LC=(TD−T0/T0)×100. (2)
Results
- 2. Mix treated virus with cells.
- 3. Measure Virus production.
- 4. Negative control: no virus in cell.
- 5. Positive control—untreated virus mixed with cell.
- Result: The virus growth is inhibited after treatments of compound of this invention.
- 1) 5 groups of rats:
- 2) 3 dose groups (low, mid, high), 1 positive control (no drug, with croton oil), 1 negative control (no drug, no croton Oil)
- 3) Give drug (Compound Y) for 7 days in 3 dose groups (low, mid, high) of rats.
- 4) On
day 7, apply croton oil to the Give-Drug-groups after giving drug. - 5) At the 24th hour after applying croton oil, isolate the recto-anus tissue (10 mm) of rats.
- 6) Apply croton oil to control group. At the 24th hour after applying croton oil, isolate the recto-anus tissue (10 mm) of rats.
- 7) Compare the swelling of give-drug-groups with positive control (no drug, with croton oil) and negative control (no drug, no croton oil).
- 8) The result shows that Compound Y inhibiting the swelling of recto-annus induced by croton oil.
- 1) 5 groups of rats:
- 2) 3 dose groups (low, mid, high), 1 positive control (no drug, with Carrageenin), 1 negative control (no drug, no Carrageenin)
- 3) Give drug (Compound Y) for 7 days in 3 dose groups (low, mid, high) of rats.
- 4) On
day 7, apply Carrageenin to the Give-Drug-groups after givingdrug 10 min. - 5) Measure the swell volume of the paw of rats at 0.5, 1, 2, 4, 6 hours after applying the Carrageenin.
- 6) Compare the swelling of give-drug-groups with positive control (no drug, with Carrageenin) and negative control (no drug, no Carrageenin).
- 7) The result shows that Compound Y inhibiting the leg swelling.
Claims (23)
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US12/541,713 US8735558B2 (en) | 2005-02-14 | 2009-08-14 | Blocking the migration or metastasis of cancer cells by affecting adhesion proteins and the uses of new compounds thereof |
US12/856,322 US8586719B2 (en) | 2005-04-27 | 2010-08-13 | Triterpenes for modulating gene expression and cell membrane, and as antiprotozoal agents |
US13/841,053 US9382285B2 (en) | 2004-09-07 | 2013-03-15 | Methods and compounds for modulating the secretion or expression of adhesion proteins or angiopoietins of cells |
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US16/285,634 US11046724B2 (en) | 2004-09-07 | 2019-02-26 | Methods and compounds for modulating the secretion or expression of adhesion proteins or angiopoietins of cells |
US17/362,028 US20220024961A1 (en) | 2004-09-07 | 2021-06-29 | Methods and compounds for modulating the secretion or expression of adhesion proteins or angiopoietins of cells |
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US10/906,303 US7524824B2 (en) | 2003-09-04 | 2005-02-14 | Composition comprising Xanthoceras sorbifolia extracts, compounds isolated from same, methods for preparing same and uses thereof |
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US11/131,551 US7262285B2 (en) | 2003-10-09 | 2005-05-17 | Anticancer biangeloyl saponins |
PCT/US2005/031900 WO2006029221A2 (en) | 2004-09-07 | 2005-09-07 | Anti-tumor compounds with angeloyl groups |
US11/267,523 US20060111310A1 (en) | 2003-10-09 | 2005-11-04 | Composition comprising triterpene saponins and compounds with angeloyl functional group, methods for preparing same and uses thereof |
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US12/344,682 US8841265B2 (en) | 2003-10-09 | 2008-12-29 | Composition comprising triterpene saponins and compounds with angeloyl functional group, methods for preparing same and uses thereof |
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PCT/US2008/002086 Continuation-In-Part WO2008133766A1 (en) | 2004-09-07 | 2008-02-15 | Blocking the migration or metastasis of cancer cells by affecting adhesion proteins and the uses of new compounds thereof |
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PCT/US2009/034115 Continuation-In-Part WO2009117196A1 (en) | 2004-09-07 | 2009-02-13 | Blocking the metastasis of cancer cells and the uses of new compounds thereof |
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WO2006116656A3 (en) | 2007-02-15 |
US7488753B2 (en) | 2009-02-10 |
WO2006116656A2 (en) | 2006-11-02 |
EP1876896A2 (en) | 2008-01-16 |
US20090156515A1 (en) | 2009-06-18 |
US20060122129A1 (en) | 2006-06-08 |
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